Download PDF
Synfacts 2009(8): 0880-0880  
DOI: 10.1055/s-0029-1217432
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Morita-Baylis-Hillman Reaction

Contributor(s): Mark Lautens, Chit Tsui
B. K. Senapati, G.-S. Hwang, S. Lee, D. H. Ryu*
Sungkyunkwan University, Suwon and Chungnam National University, Seoul, Korea
Further Information

Publication History

Publication Date:
23 July 2009 (online)

    Permissions and Reprints

Significance

This report describes a highly enantioselective and Z-stereocontrolled three-component coupling of α,β-acetylenic esters, aldehydes, and trimethylsilyl iodide (TMSI) using chiral cationic oxazaborolidinium catalysts. Both enantiomers (R/S) of the (Z)-β-iodo Morita-Baylis-Hillman (MBH) ester product could be obtained enantioselectively by using the chiral catalysts 1a and its enantiomer. The subsequent metal-catalyzed cross-coupling of these esters were performed directly with retention of configuration to afford synthetically more useful β-branched MBH esters.