Anti- and Syn-Selective Cyanosilylation Reactions Promoted by a Sugar-Based Bifunctional Catalyst: Stereoselective Syntheses of Essential Building Blocks for HIV Protease Inhibitors and Bestatin

Govindaswamy Manickam; Hiroyuki Nogami; Motomu Kanai; Harald Gröger; Masakatsu Shibasaki

doi:10.1055/s-2001-13383

Synlett 2001; 2001(5): 0617-0620
DOI: 10.1055/s-2001-13383

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Anti- and Syn-Selective Cyanosilylation Reactions Promoted by a Sugar-Based Bifunctional Catalyst: Stereoselective Syntheses of Essential Building Blocks for HIV Protease Inhibitors and Bestatin

Govindaswamy Manickam^* , Hiroyuki Nogami, Motomu Kanai, Harald Gröger, Masakatsu Shibasaki

^*Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan; Fax + 81-3-5684-5206; E-mail: mshibasa@mol.f.u-tokyo.ac.jp

Abstract

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Chiral bifunctional catalyst 6 promoted anti- and syn-selective cyanosilylation reactions from chiral amino aldehydes derived from phenylalanine in excellent yields. Thus, from dibenzyl protected amino aldehyde 9, syn isomer was obtained as the major product (diastereomeric ratio = 93 : 7) using 3 mol% of 6. On the other hand, from Boc protected aldehyde 10, anti isomer was obtained as the major product (diastereomeric ratio = 97 : 3) by 1 mol% of 6. The experimental results can be rationally explained from the dual activation mechanism of 6. Using syn- and anti-selective cyanosilylation reactions, efficient syntheses of essential chiral building blocks of HIV protease inhibitors and bestatin were achieved.

bifunctional catalyst - cyanosilylation - amino aldehyde - HIV protease inhibitors - bestatin

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