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Communication | Special issue | Vol 73, No. 1, 2007, pp.191-195
Published online, 10th August, 2007
DOI: 10.3987/COM-07-S(U)25
Diastereoselective Approach to an HIV Protease Inhibitor Intermediate Using a Cation-Exchange Resin Mediated Mannich-Type Reaction

Makoto Shimizu,* Yukinori Hayashi, Ryosuke Hamanaka, and Iwao Hachiya

*Department of Chemistry for Materials, Graduate School of Engineering, Mie University, Tsu, Mie 514-8507, Japan

Abstract

Mannich-type reaction of ketene silyl acetals with a chiral imine proceeded smoothly to give β-amino esters in good yields with high diasetereoselectivity under the influence of a cation-exchange resin, and the subsequent functional group transformations gave an HIV protease inhibitor intermediate.