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Formation of Macrocyclic Lactones by Enantioselective Intramolecular Cyclopropanation of Diazoacetates Catalyzed by Chiral Cu I and Rh II Compounds

1996; Wiley; Volume: 35; Issue: 12 Linguagem: Inglês

10.1002/anie.199613341

1521-3773

Michael P. Doyle, Chad S. Peterson, Dann L. Parker,

Asymmetric Hydrogenation and Catalysis

Angewandte Chemie International Edition in EnglishVolume 35, Issue 12 p. 1334-1336 Communication Formation of Macrocyclic Lactones by Enantioselective Intramolecular Cyclopropanation of Diazoacetates Catalyzed by Chiral CuI and RhII Compounds† Prof. Michael P. Doyle, Corresponding Author Prof. Michael P. Doyle Department of Chemistry, Trinity University, San Antonio, TX 78212-7200 (USA), Fax: Int. code +(210)736-7569, e-mail: mdoyle@trinity.eduDepartment of Chemistry, Trinity University, San Antonio, TX 78212-7200 (USA), Fax: Int. code +(210)736-7569, e-mail: mdoyle@trinity.eduSearch for more papers by this authorDr. Chad S. Peterson, Dr. Chad S. Peterson Department of Chemistry, Trinity University, San Antonio, TX 78212-7200 (USA), Fax: Int. code +(210)736-7569, e-mail: mdoyle@trinity.eduSearch for more papers by this authorDann L. Parker Jr., Dann L. Parker Jr. Department of Chemistry, Trinity University, San Antonio, TX 78212-7200 (USA), Fax: Int. code +(210)736-7569, e-mail: mdoyle@trinity.eduSearch for more papers by this author Prof. Michael P. Doyle, Corresponding Author Prof. Michael P. Doyle Department of Chemistry, Trinity University, San Antonio, TX 78212-7200 (USA), Fax: Int. code +(210)736-7569, e-mail: mdoyle@trinity.eduDepartment of Chemistry, Trinity University, San Antonio, TX 78212-7200 (USA), Fax: Int. code +(210)736-7569, e-mail: mdoyle@trinity.eduSearch for more papers by this authorDr. Chad S. Peterson, Dr. Chad S. Peterson Department of Chemistry, Trinity University, San Antonio, TX 78212-7200 (USA), Fax: Int. code +(210)736-7569, e-mail: mdoyle@trinity.eduSearch for more papers by this authorDann L. Parker Jr., Dann L. Parker Jr. Department of Chemistry, Trinity University, San Antonio, TX 78212-7200 (USA), Fax: Int. code +(210)736-7569, e-mail: mdoyle@trinity.eduSearch for more papers by this author First published: July 9, 1996 https://doi.org/10.1002/anie.199613341Citations: 77 † This work was supported by grants from the Robert A. Welch Foundation and the National Science Foundation. AboutPDF 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 onFacebookTwitterLinked InRedditWechat Abstract A new method for the catalytic asymmetric synthesis of macrocycles is based on the intramolecular cyclopropanation of long-chain diazoacetates containing a double bond. Thus, for example, with [Cu(MeCN)4](PF6) in the presence of a chiral bis(dihydrooxazole) ligand, the 15-membered ring lactone 1 was formed not only with excellent regioselectivity (ratio of 15-membered to 10-membered ring is 25:1) but also with remarkably high enantioselectivity (90% ee). Citing Literature Volume35, Issue12July 9, 1996Pages 1334-1336 RelatedInformation