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Highly diastereoselective synthesis of vicinal quaternary and tertiary stereocenters using the iodo-aldol cyclization.

作者信息

Douelle Frederic, Capes Amy S, Greaney Michael F

机构信息

University of Edinburgh, School of Chemistry, Joseph Black Building, King's Buildings, Edinburgh, UK.

出版信息

Org Lett. 2007 May 10;9(10):1931-4. doi: 10.1021/ol070482k. Epub 2007 Apr 11.

DOI:10.1021/ol070482k
PMID:17425327
Abstract

The intramolecular iodo-aldol cyclization of alpha-substituted enoate aldehydes and ketones is described. Using prochiral starting materials, the reaction produces hetero- and carbocycles containing quaternary centers adjacent to secondary or tertiary centers. The reactions occur in good yields and are highly selective for the trans-products, having the hydroxyl and iodomethyl groups on opposite faces of the ring system.

摘要

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