Highly Diastereoselective Synthesis of vicinal Quaternary and Tertiary Stereocenters Using the Iodo-aldol Cyclization

The intramolecular iodo-aldol cyclization of α-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...

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Bibliographic Details
Published in:Organic letters 2007-05, Vol.9 (10), p.1931-1934
Main Authors: Douelle, Frederic, Capes, Amy S, Greaney, Michael F
Format: Article
Language:English
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Summary:The intramolecular iodo-aldol cyclization of α-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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol070482k