Highly diastereoselective synthesis of vicinal quaternary and tertiary stereocenters using the iodo-aldol cyclization.
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.
Douelle
Frederic
F
University of Edinburgh, School of Chemistry, Joseph Black Building, King's Buildings, Edinburgh, UK.
Capes
Amy S
AS
Greaney
Michael F
MF