Enantiopure 1,4-Diols and 1,4-Aminoalcohols via Stereoselective Acyclic Sulfoxide−Sulfenate Rearrangement

Name: Work Video:
Duration: 3 min 30 s
Description: Treatment of acyclic α-hydroxy and α-tosylamino sulfinyl dienes with amines affords enantiopure 1,4-diol or 1,4-hydroxysulfonamide derivatives in good yields and diastereoselectivities. This one-pot procedure entails a conjugate addition that triggers a diastereoselective sulfoxide−sulfenate [2,3]-sigmatropic rearrangement.
Roberto Fernández de la Pradilla; Ignacio Colomer; Mercedes Ureña; Alma Viso
{'id': 'https://openalex.org/W2316432698', 'doi': 'https://doi.org/10.1021/ol200718y', 'title': 'Enantiopure 1,4-Diols and 1,4-Aminoalcohols via Stereoselective Acyclic Sulfoxide−Sulfenate Rearrangement', 'display_name': 'Enantiopure 1,4-Diols and 1,4-Aminoalcohols via Stereoselective Acyclic Sulfoxide−Sulfenate Rearrangement', 'publication_year': 2011, 'publication_date': '2011-04-06', 'ids': {'openalex': 'https://openalex.org/W2316432698', 'doi': 'https://doi.org/10.1021/ol200718y', 'mag': '2316432698', 'pmid': 'https://pubmed.ncbi.nlm.nih.gov/21469662'}, 'language': 'en', 'primary_location': {'is_oa': False, 'landing_page_url': 'https://doi.org/10.1021/ol200718y', 'pdf_url': None, 'source': {'id': 'https://openalex.org/S201989124', 'display_name': 'Organic Letters', 'issn_l': '1523-7052', 'issn': ['1523-7052', '1523-7060'], 'is_oa': False, 'is_in_doaj': False, 'is_indexed_in_scopus': True, 'is_core': True, 'host_organization': 'https://openalex.org/P4310320006', 'host_organization_name': 'American Chemical Society', 'host_organization_lineage': ['https://openalex.org/P4310320006'], 'host_organization_lineage_names': ['American Chemical Society'], 'type': 'journal'}, 'license': None, 'license_id': None, 'version': None, 'is_accepted': False, 'is_published': False}, 'type': 'article', 'type_crossref': 'journal-article', 'indexed_in': ['crossref', 'pubmed'], 'open_access': {'is_oa': False, 'oa_status': 'closed', 'oa_url': None, 'any_repository_has_fulltext': False}, 'authorships': [{'author_position': 'first', 'author': {'id': 'https://openalex.org/A5071811984', 'display_name': 'Roberto Fernández de la Pradilla', 'orcid': 'https://orcid.org/0000-0002-6633-8499'}, 'institutions': [{'id': 'https://openalex.org/I4210162082', 'display_name': 'Instituto de Química Orgánica General', 'ror': 'https://ror.org/05e0q7s59', 'country_code': 'ES', 'type': 'facility', 'lineage': ['https://openalex.org/I134820265', 'https://openalex.org/I4210162082']}], 'countries': ['ES'], 'is_corresponding': False, 'raw_author_name': 'Roberto Fernández de la Pradilla', 'raw_affiliation_strings': ['Instituto de Química Orgánica General, IQOG-CSIC. Juan de la Cierva 3, 28006 Madrid, Spain'], 'affiliations': [{'raw_affiliation_string': 'Instituto de Química Orgánica General, IQOG-CSIC. Juan de la Cierva 3, 28006 Madrid, Spain', 'institution_ids': ['https://openalex.org/I4210162082']}]}, {'author_position': 'middle', 'author': {'id': 'https://openalex.org/A5059129535', 'display_name': 'Ignacio Colomer', 'orcid': 'https://orcid.org/0000-0001-5542-7034'}, 'institutions': [{'id': 'https://openalex.org/I4210162082', 'display_name': 'Instituto de Química Orgánica General', 'ror': 'https://ror.org/05e0q7s59', 'country_code': 'ES', 'type': 'facility', 'lineage': ['https://openalex.org/I134820265', 'https://openalex.org/I4210162082']}], 'countries': ['ES'], 'is_corresponding': False, 'raw_author_name': 'Ignacio Colomer', 'raw_affiliation_strings': ['Instituto de Química Orgánica General, IQOG-CSIC. Juan de la Cierva 3, 28006 Madrid, Spain'], 'affiliations': [{'raw_affiliation_string': 'Instituto de Química Orgánica General, IQOG-CSIC. Juan de la Cierva 3, 28006 Madrid, Spain', 'institution_ids': ['https://openalex.org/I4210162082']}]}, {'author_position': 'middle', 'author': {'id': 'https://openalex.org/A5036305825', 'display_name': 'Mercedes Ureña', 'orcid': None}, 'institutions': [{'id': 'https://openalex.org/I4210162082', 'display_name': 'Instituto de Química Orgánica General', 'ror': 'https://ror.org/05e0q7s59', 'country_code': 'ES', 'type': 'facility', 'lineage': ['https://openalex.org/I134820265', 'https://openalex.org/I4210162082']}], 'countries': ['ES'], 'is_corresponding': False, 'raw_author_name': 'Mercedes Ureña', 'raw_affiliation_strings': ['Instituto de Química Orgánica General, IQOG-CSIC. Juan de la Cierva 3, 28006 Madrid, Spain'], 'affiliations': [{'raw_affiliation_string': 'Instituto de Química Orgánica General, IQOG-CSIC. Juan de la Cierva 3, 28006 Madrid, Spain', 'institution_ids': ['https://openalex.org/I4210162082']}]}, {'author_position': 'last', 'author': {'id': 'https://openalex.org/A5073920549', 'display_name': 'Alma Viso', 'orcid': 'https://orcid.org/0000-0003-2622-4777'}, 'institutions': [{'id': 'https://openalex.org/I4210162082', 'display_name': 'Instituto de Química Orgánica General', 'ror': 'https://ror.org/05e0q7s59', 'country_code': 'ES', 'type': 'facility', 'lineage': ['https://openalex.org/I134820265', 'https://openalex.org/I4210162082']}], 'countries': ['ES'], 'is_corresponding': False, 'raw_author_name': 'Alma Viso', 'raw_affiliation_strings': ['Instituto de Química Orgánica General, IQOG-CSIC. Juan de la Cierva 3, 28006 Madrid, Spain'], 'affiliations': [{'raw_affiliation_string': 'Instituto de Química Orgánica General, IQOG-CSIC. Juan de la Cierva 3, 28006 Madrid, Spain', 'institution_ids': ['https://openalex.org/I4210162082']}]}], 'institution_assertions': [], 'countries_distinct_count': 1, 'institutions_distinct_count': 1, 'corresponding_author_ids': [], 'corresponding_institution_ids': [], 'apc_list': None, 'apc_paid': None, 'fwci': 1.373, 'has_fulltext': True, 'fulltext_origin': 'ngrams', 'cited_by_count': 23, 'citation_normalized_percentile': {'value': 0.782815, 'is_in_top_1_percent': False, 'is_in_top_10_percent': False}, 'cited_by_percentile_year': {'min': 90, 'max': 91}, 'biblio': {'volume': '13', 'issue': '9', 'first_page': '2468', 'last_page': '2471'}, 'is_retracted': False, 'is_paratext': False, 'primary_topic': {'id': 'https://openalex.org/T12189', 'display_name': 'Sulfur-Based Synthesis Techniques', 'score': 0.9998, 'subfield': {'id': 'https://openalex.org/subfields/1605', 'display_name': 'Organic Chemistry'}, 'field': {'id': 'https://openalex.org/fields/16', 'display_name': 'Chemistry'}, 'domain': {'id': 'https://openalex.org/domains/3', 'display_name': 'Physical Sciences'}}, 'topics': [{'id': 'https://openalex.org/T12189', 'display_name': 'Sulfur-Based Synthesis Techniques', 'score': 0.9998, 'subfield': {'id': 'https://openalex.org/subfields/1605', 'display_name': 'Organic Chemistry'}, 'field': {'id': 'https://openalex.org/fields/16', 'display_name': 'Chemistry'}, 'domain': {'id': 'https://openalex.org/domains/3', 'display_name': 'Physical Sciences'}}, {'id': 'https://openalex.org/T10013', 'display_name': 'Asymmetric Synthesis and Catalysis', 'score': 0.9996, 'subfield': {'id': 'https://openalex.org/subfields/1605', 'display_name': 'Organic Chemistry'}, 'field': {'id': 'https://openalex.org/fields/16', 'display_name': 'Chemistry'}, 'domain': {'id': 'https://openalex.org/domains/3', 'display_name': 'Physical Sciences'}}, {'id': 'https://openalex.org/T12251', 'display_name': 'Synthesis and Catalytic Reactions', 'score': 0.9995, 'subfield': {'id': 'https://openalex.org/subfields/1605', 'display_name': 'Organic Chemistry'}, 'field': {'id': 'https://openalex.org/fields/16', 'display_name': 'Chemistry'}, 'domain': {'id': 'https://openalex.org/domains/3', 'display_name': 'Physical Sciences'}}], 'keywords': [{'id': 'https://openalex.org/keywords/enantiopure-drug', 'display_name': 'Enantiopure drug', 'score': 0.9861288}, {'id': 'https://openalex.org/keywords/sulfoxide', 'display_name': 'Sulfoxide', 'score': 0.830088}], 'concepts': [{'id': 'https://openalex.org/C93237805', 'wikidata': 'https://www.wikidata.org/wiki/Q5375227', 'display_name': 'Enantiopure drug', 'level': 4, 'score': 0.9861288}, {'id': 'https://openalex.org/C185592680', 'wikidata': 'https://www.wikidata.org/wiki/Q2329', 'display_name': 'Chemistry', 'level': 0, 'score': 0.86976707}, {'id': 'https://openalex.org/C181647583', 'wikidata': 'https://www.wikidata.org/wiki/Q903429', 'display_name': 'Stereoselectivity', 'level': 3, 'score': 0.85654193}, {'id': 'https://openalex.org/C2778448320', 'wikidata': 'https://www.wikidata.org/wiki/Q408395', 'display_name': 'Sulfoxide', 'level': 2, 'score': 0.830088}, {'id': 'https://openalex.org/C71240020', 'wikidata': 'https://www.wikidata.org/wiki/Q186011', 'display_name': 'Stereochemistry', 'level': 1, 'score': 0.4113286}, {'id': 'https://openalex.org/C178790620', 'wikidata': 'https://www.wikidata.org/wiki/Q11351', 'display_name': 'Organic chemistry', 'level': 1, 'score': 0.27718556}, {'id': 'https://openalex.org/C146686406', 'wikidata': 'https://www.wikidata.org/wiki/Q898628', 'display_name': 'Enantioselective synthesis', 'level': 3, 'score': 0.13008663}, {'id': 'https://openalex.org/C161790260', 'wikidata': 'https://www.wikidata.org/wiki/Q82264', 'display_name': 'Catalysis', 'level': 2, 'score': 0.08878109}], 'mesh': [{'descriptor_ui': 'D000438', 'descriptor_name': 'Alcohols', 'qualifier_ui': 'Q000138', 'qualifier_name': 'chemical synthesis', 'is_major_topic': True}, {'descriptor_ui': 'D012451', 'descriptor_name': 'Safrole', 'qualifier_ui': 'Q000031', 'qualifier_name': 'analogs & derivatives', 'is_major_topic': True}, {'descriptor_ui': 'D013434', 'descriptor_name': 'Sulfenic Acids', 'qualifier_ui': 'Q000737', 'qualifier_name': 'chemistry', 'is_major_topic': True}, {'descriptor_ui': 'D013454', 'descriptor_name': 'Sulfoxides', 'qualifier_ui': 'Q000737', 'qualifier_name': 'chemistry', 'is_major_topic': True}, {'descriptor_ui': 'D000438', 'descriptor_name': 'Alcohols', 'qualifier_ui': '', 'qualifier_name': None, 'is_major_topic': False}, {'descriptor_ui': 'D000586', 'descriptor_name': 'Amination', 'qualifier_ui': '', 'qualifier_name': None, 'is_major_topic': False}, {'descriptor_ui': 'D015394', 'descriptor_name': 'Molecular Structure', 'qualifier_ui': '', 'qualifier_name': None, 'is_major_topic': False}, {'descriptor_ui': 'D012451', 'descriptor_name': 'Safrole', 'qualifier_ui': 'Q000737', 'qualifier_name': 'chemistry', 'is_major_topic': False}, {'descriptor_ui': 'D012451', 'descriptor_name': 'Safrole', 'qualifier_ui': '', 'qualifier_name': None, 'is_major_topic': False}, {'descriptor_ui': 'D013237', 'descriptor_name': 'Stereoisomerism', 'qualifier_ui': '', 'qualifier_name': None, 'is_major_topic': False}, {'descriptor_ui': 'D013434', 'descriptor_name': 'Sulfenic Acids', 'qualifier_ui': '', 'qualifier_name': None, 'is_major_topic': False}, {'descriptor_ui': 'D013454', 'descriptor_name': 'Sulfoxides', 'qualifier_ui': '', 'qualifier_name': None, 'is_major_topic': False}], 'locations_count': 2, 'locations': [{'is_oa': False, 'landing_page_url': 'https://doi.org/10.1021/ol200718y', 'pdf_url': None, 'source': {'id': 'https://openalex.org/S201989124', 'display_name': 'Organic Letters', 'issn_l': '1523-7052', 'issn': ['1523-7052', '1523-7060'], 'is_oa': False, 'is_in_doaj': False, 'is_indexed_in_scopus': True, 'is_core': True, 'host_organization': 'https://openalex.org/P4310320006', 'host_organization_name': 'American Chemical Society', 'host_organization_lineage': ['https://openalex.org/P4310320006'], 'host_organization_lineage_names': ['American Chemical Society'], 'type': 'journal'}, 'license': None, 'license_id': None, 'version': None, 'is_accepted': False, 'is_published': False}, {'is_oa': False, 'landing_page_url': 'https://pubmed.ncbi.nlm.nih.gov/21469662', 'pdf_url': None, 'source': {'id': 'https://openalex.org/S4306525036', 'display_name': 'PubMed', 'issn_l': None, 'issn': None, 'is_oa': False, 'is_in_doaj': False, 'is_indexed_in_scopus': False, 'is_core': False, 'host_organization': 'https://openalex.org/I1299303238', 'host_organization_name': 'National Institutes of Health', 'host_organization_lineage': ['https://openalex.org/I1299303238'], 'host_organization_lineage_names': ['National Institutes of Health'], 'type': 'repository'}, 'license': None, 'license_id': None, 'version': None, 'is_accepted': False, 'is_published': False}], 'best_oa_location': None, 'sustainable_development_goals': [{'display_name': 'Clean water and sanitation', 'score': 0.41, 'id': 'https://metadata.un.org/sdg/6'}], 'grants': [], 'datasets': [], 'versions': [], 'referenced_works_count': 59, 'referenced_works': ['https://openalex.org/W1967630134', 'https://openalex.org/W1968932636', 'https://openalex.org/W1971874689', 'https://openalex.org/W1973327120', 'https://openalex.org/W1976538508', 'https://openalex.org/W1976580458', 'https://openalex.org/W1977222013', 'https://openalex.org/W1978529340', 'https://openalex.org/W1982612425', 'https://openalex.org/W1986709322', 'https://openalex.org/W1989796497', 'https://openalex.org/W1995017886', 'https://openalex.org/W2003867194', 'https://openalex.org/W2006849824', 'https://openalex.org/W2007412729', 'https://openalex.org/W2007989887', 'https://openalex.org/W2017821091', 'https://openalex.org/W2029008705', 'https://openalex.org/W2033493758', 'https://openalex.org/W2034795876', 'https://openalex.org/W2038489510', 'https://openalex.org/W2039959812', 'https://openalex.org/W2044530829', 'https://openalex.org/W2060521583', 'https://openalex.org/W2061604313', 'https://openalex.org/W2064823771', 'https://openalex.org/W2070348642', 'https://openalex.org/W2077825098', 'https://openalex.org/W2078288151', 'https://openalex.org/W2078363818', 'https://openalex.org/W2088864691', 'https://openalex.org/W2091140455', 'https://openalex.org/W2121521502', 'https://openalex.org/W2127350928', 'https://openalex.org/W2127548847', 'https://openalex.org/W2130199568', 'https://openalex.org/W2137704024', 'https://openalex.org/W2143023054', 'https://openalex.org/W2161484915', 'https://openalex.org/W2162188532', 'https://openalex.org/W2165411454', 'https://openalex.org/W2322601513', 'https://openalex.org/W2949517642', 'https://openalex.org/W2949758833', 'https://openalex.org/W2949808010', 'https://openalex.org/W2949997708', 'https://openalex.org/W2950192436', 'https://openalex.org/W2950244758', 'https://openalex.org/W2950439740', 'https://openalex.org/W2950767788', 'https://openalex.org/W2950957774', 'https://openalex.org/W2950967761', 'https://openalex.org/W2951037936', 'https://openalex.org/W2951288129', 'https://openalex.org/W2951465343', 'https://openalex.org/W2952380155', 'https://openalex.org/W2953133720', 'https://openalex.org/W2953327637', 'https://openalex.org/W4247647646'], 'related_works': ['https://openalex.org/W4391375266', 'https://openalex.org/W3214687586', 'https://openalex.org/W2952090861', 'https://openalex.org/W2949257144', 'https://openalex.org/W2948807893', 'https://openalex.org/W2778153218', 'https://openalex.org/W2748952813', 'https://openalex.org/W2316432698', 'https://openalex.org/W2053616378', 'https://openalex.org/W2011903922'], 'abstract_inverted_index': {'Treatment': [0], 'of': [1], 'acyclic': [2], 'α-hydroxy': [3], 'and': [4, 19], 'α-tosylamino': [5], 'sulfinyl': [6], 'dienes': [7], 'with': [8], 'amines': [9], 'affords': [10], 'enantiopure': [11], '1,4-diol': [12], 'or': [13], '1,4-hydroxysulfonamide': [14], 'derivatives': [15], 'in': [16], 'good': [17], 'yields': [18], 'diastereoselectivities.': [20], 'This': [21], 'one-pot': [22], 'procedure': [23], 'entails': [24], 'a': [25, 30], 'conjugate': [26], 'addition': [27], 'that': [28], 'triggers': [29], 'diastereoselective': [31], 'sulfoxide−sulfenate': [32], '[2,3]-sigmatropic': [33], 'rearrangement.': [34]}, 'abstract_inverted_index_v3': None, 'cited_by_api_url': 'https://api.openalex.org/works?filter=cites:W2316432698', 'counts_by_year': [{'year': 2023, 'cited_by_count': 2}, {'year': 2021, 'cited_by_count': 1}, {'year': 2020, 'cited_by_count': 2}, {'year': 2019, 'cited_by_count': 1}, {'year': 2017, 'cited_by_count': 3}, {'year': 2016, 'cited_by_count': 1}, {'year': 2015, 'cited_by_count': 4}, {'year': 2014, 'cited_by_count': 5}, {'year': 2013, 'cited_by_count': 2}, {'year': 2012, 'cited_by_count': 1}], 'updated_date': '2025-01-17T07:40:36.944488', 'created_date': '2016-06-24'}
Publication Information

Basic Information

Access and Citation

AI Researcher Chatbot

Primary Location

Authors

Topics

Keywords

Related Works
