Reagent control in the aldol addition reaction of chiral boron enolates with chiral aldehydes. Total synthesis of (3S,4S)-statine

被引：22

作者：

Gennari, C

Moresca, D

Vulpetti, A

Pain, G

机构：

[1] Dip. di Chim. Organica e Industriale, Universita' di Milano, Centro CNR Sost.Org.Nat., via Venezian 21

[2] Clariant, Palazzolo Milanese (Milano)

[3] Pharmacia and Upjohn, Nerviano (Milano)

[4] Glaxo-Wellcome, Verona

来源：

TETRAHEDRON | 1997年 / 53卷 / 15期

关键词：

D O I：

10.1016/S0040-4020(97)00215-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Boron enolates bearing menthone-derived chiral ligands are capable of fair to excellent diastereocontrol in their reactions with chiral aldehydes. Thioester-derived (better than ketone derived) enolates are able to control aldol stereochemistry irrespective of the aldehyde preferences. With thioacetate-derived chiral enolates and enantiopure N,N-dibenzyl alpha-amino aldehydes, either the 3,4-anti or the 3,4-syn aldol adduct can be obtained with very high diastereoselectivity just by changing the chiral boron ligand configuration. The above procedure was used for a stereoselective total synthesis of (3S, 4S)-statine. (C) 1997 Elsevier Science Ltd.

引用

页码：5593 / 5608

页数：16

共 59 条

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