Tetrahedron

Stereoselective synthesis of (3R, 4S)-statine utilising the iron acetyl complex [(η 5-C 5 H 5) Fe (CO)(PPh 3) COMe] as a chiral acetate enolate equivalent.

JWB Cooke, SG Davies, A Naylor

Index: Cooke, Jason W. B.; Davies, Stephen G.; Naylor, Alan Tetrahedron, 1993 , vol. 49, # 36 p. 7955 - 7966

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Citation Number: 36

Abstract

Diethylaluminium enolates derived from the iron acetyl complex [(η5-C5H5) Fe (CO)(PPh3) COMe] undergo highly diastereoselective aldol reactions with the homochiral aldehydes; N, N-dibenzyl valinal and N, N-dibenzyl leucinal. The diastereoselectivity is explained in terms of Masamune's model of double asymmetric induction using the concept of matched and mismatched pairs. The matched pair aldol product arising from the reaction with N, N- ...