ASYMMETRIC HETERO DIELS-ALDER REACTIONS OF DANISHEFSKY'S DIENE AND GLYOXYLATE ESTERS CATALYZED BY CHIRAL BISOXAZOLINE DERIVED CATALYSTS

Arun K Ghosh; Packiarajan Mathivanan; John Cappiello; K Krishnan

doi:10.1016/0957-4166(96)00261-3

ASYMMETRIC HETERO DIELS-ALDER REACTIONS OF DANISHEFSKY'S DIENE AND GLYOXYLATE ESTERS CATALYZED BY CHIRAL BISOXAZOLINE DERIVED CATALYSTS

Tetrahedron Asymmetry. 1996 Aug;7(8):2165-2168. doi: 10.1016/0957-4166(96)00261-3.

Authors

Arun K Ghosh¹, Packiarajan Mathivanan¹, John Cappiello¹, K Krishnan¹

Affiliation

¹ Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607.

Abstract

Asymmetric hetero Diels-Alder reactions of Danishefsky's diene and glyoxylate esters catalyzed by bis(oxazoline)-metal complex afforded the corresponding aldol adduct which upon treatment with trifluoroacetic acid furnished the hetero Diels-Alder product in 72% enantiomeric excess and 70% isolated yield.

Abstract

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