Title: Highly Enantioselective Preparation of Tertiary Alcohols and Amines by Copper‐Mediated Diastereoselective Allylic S<sub>N</sub>2′ Substitutions
Abstract: Angewandte Chemie International EditionVolume 44, Issue 29 p. 4627-4631 Communication Highly Enantioselective Preparation of Tertiary Alcohols and Amines by Copper-Mediated Diastereoselective Allylic SN2′ Substitutions† Helena Leuser Dr., Helena Leuser Dr. Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5–13, Haus F, 81377 München, Germany, Fax: (+49) 89-2180-77680Search for more papers by this authorSylvie Perrone Dipl.-Chem., Sylvie Perrone Dipl.-Chem. Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5–13, Haus F, 81377 München, Germany, Fax: (+49) 89-2180-77680Search for more papers by this authorFrédéric Liron Dr., Frédéric Liron Dr. Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5–13, Haus F, 81377 München, Germany, Fax: (+49) 89-2180-77680Search for more papers by this authorFlorian F. Kneisel Dr., Florian F. Kneisel Dr. Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5–13, Haus F, 81377 München, Germany, Fax: (+49) 89-2180-77680Search for more papers by this authorPaul Knochel Prof. Dr., Paul Knochel Prof. Dr. [email protected] Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5–13, Haus F, 81377 München, Germany, Fax: (+49) 89-2180-77680Search for more papers by this author Helena Leuser Dr., Helena Leuser Dr. Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5–13, Haus F, 81377 München, Germany, Fax: (+49) 89-2180-77680Search for more papers by this authorSylvie Perrone Dipl.-Chem., Sylvie Perrone Dipl.-Chem. Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5–13, Haus F, 81377 München, Germany, Fax: (+49) 89-2180-77680Search for more papers by this authorFrédéric Liron Dr., Frédéric Liron Dr. Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5–13, Haus F, 81377 München, Germany, Fax: (+49) 89-2180-77680Search for more papers by this authorFlorian F. Kneisel Dr., Florian F. Kneisel Dr. Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5–13, Haus F, 81377 München, Germany, Fax: (+49) 89-2180-77680Search for more papers by this authorPaul Knochel Prof. Dr., Paul Knochel Prof. Dr. [email protected] Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5–13, Haus F, 81377 München, Germany, Fax: (+49) 89-2180-77680Search for more papers by this author First published: 08 July 2005 https://doi.org/10.1002/anie.200500672Citations: 73 † We thank the Fonds der Chemischen Industrie, the Deutsche Forschungsgemeinschaft (DFG), and Merck Research Laboratories (MSD) for financial support. We also thank Chemetall GmbH (Frankfurt) and BASF AG (Ludwigshafen) for generous gifts of chemicals. Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract Trisubstituted allylic pentafluorobenzoates react with diorganozinc reagents in the presence of CuCN⋅2 LiCl to provide alkenes bearing a chiral quaternary center in α position (>95 % ee). These alkenes are readily converted into chiral tertiary alcohols or into chiral amino alcohols by a straightforward sequence of ozonolysis followed by Curtius rearrangement (see scheme). Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2005/z500672_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. References 1 1aD. J. Ramon, M. Yus, Angew. Chem. 2004, 116, 286; Angew. Chem. Int. Ed. 2004, 43, 284; 1bB. Weber, D. Seebach, Angew. Chem. 1992, 104, 96; Angew. Chem. Int. Ed. Engl. 1992, 31, 84; 1cB. Weber, D. Seebach, Tetrahedron 1994, 50, 6117; 1dP. I. Dosa, G. C. Fu, J. Am. Chem. Soc. 1998, 120, 445; 1eC. Bolm, J. P. Hildebrand, K. Muniz, N. Hermanns, Angew. Chem. 2001, 113, 3382; Angew. Chem. Int. Ed. 2001, 40, 3284; 1fP. G. Cozzi, Angew. Chem. 2003, 115, 3001; Angew. Chem. Int. Ed. 2003, 42, 2895; 1gB. Jiang, Z. Chen, X. Tang, Org. Lett. 2002, 4, 3451; 1hD. J. Ramon, M. 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Publication Year: 2005
Publication Date: 2005-07-08
Language: en
Type: article
Indexed In: ['crossref', 'pubmed']
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