Highly stereoselective intermolecular oxy-michael addition reaction to alpha,beta-unsaturated malonate esters.
[reaction: see text] The highly diastereoselective oxy-Michael addition of the "naked" anion of (6S)-methyl delta lactol to alkylidiene-, arylidene-, and heteroarylidenemalonate derivatives leading to the direct formation of THP-protected beta-hydroxy ester derivatives is described. Subsequent acid-mediated deprotection affords the enantioenriched aldol products in quantitative yields.
Buchanan
David J
DJ
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, U.K. djb26@cam.ac.uk
Dixon
Darren J
DJ
Hernandez-Juan
Felix A
FA