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

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Abstract

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. © 2007 American Chemical Society.

Bibliographical metadata

Original languageEnglish
Pages (from-to)1931-1934
Number of pages3
JournalOrganic Letters
Volume9
Issue number10
DOIs
StatePublished - 10 May 2007