Title: Highly Stereoselective Synthesis of Substituted γ‐Lactams from Acylsilanes
Abstract: Angewandte Chemie International EditionVolume 47, Issue 12 p. 2294-2297 Communication Highly Stereoselective Synthesis of Substituted γ-Lactams from Acylsilanes† Robert B. Lettan II, Robert B. Lettan II Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208, USA, Fax: (+1) 847-467-2184Search for more papers by this authorChase C. Woodward, Chase C. Woodward Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208, USA, Fax: (+1) 847-467-2184Search for more papers by this authorKarl A. Scheidt Prof., Karl A. Scheidt Prof. [email protected] Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208, USA, Fax: (+1) 847-467-2184Search for more papers by this author Robert B. Lettan II, Robert B. Lettan II Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208, USA, Fax: (+1) 847-467-2184Search for more papers by this authorChase C. Woodward, Chase C. Woodward Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208, USA, Fax: (+1) 847-467-2184Search for more papers by this authorKarl A. Scheidt Prof., Karl A. Scheidt Prof. [email protected] Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208, USA, Fax: (+1) 847-467-2184Search for more papers by this author First published: 03 March 2008 https://doi.org/10.1002/anie.200705229Citations: 59 † Support has been provided in part by the NSF (CHE-0348979), the PRF (Type G), and Northwestern University. We thank Abbott Laboratories, Amgen, AstraZeneca, GlaxoSmithKline, 3M, and Boehringer-Ingelheim for generous unrestricted research support, Wacker Chemical Corp. and FMCLithium for providing reagents, and Troy Reynolds (NU) for assistance with X-ray crystallography. K.A.S. is a fellow of the Alfred P. Sloan Foundation. 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 It takes three: The stereoselective synthesis of highly substituted γ-lactams from amide enolates, acylsilanes, and imines is reported. This multicomponent reaction accesses γ-amino-β-hydroxy amides in a single flask with good yields and excellent levels of diastereoselectivity (see scheme). Exposure of the linear products to microwave irradiation and acidic conditions promotes a cyclization to form the corresponding γ-lactams in excellent yields. Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2008/z705229_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 1P. A. Reddy, B. C. H. Hsiang, T. N. Latifi, M. W. Hill, K. E. Woodward, S. M. Rothman, J. A. Ferrendelli, D. F. Covey, J. Med. Chem. 1996, 39, 1898. 2K. Das Sarma, J. Zhang, Y. Huang, J. G. Davidson, Eur. J. Org. Chem. 2006, 3730. 3A. Spaltenstein, M. R. Almond, W. J. Bock, D. G. Cleary, E. S. Furfine, R. J. Hazen, W. M. Kazmierski, F. G. Salituro, R. D. Tung, L. L. Wright, Bioorg. Med. Chem. 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These data can be obtained free of charge from The Cambridge Crystallographic Data Centre at www.ccdc.cam.ac.uk/data_request/cif. Citing Literature Volume47, Issue12March 7, 2008Pages 2294-2297 ReferencesRelatedInformation