Enantioselective acyclic stereoselection under catalyst control. 4 - Novel diastereo- and enantioselectivities in the chiral oxazaborolidinone-promoted asymmetric aldol reaction of highly hindered aldehydes having a quaternary carbon at a position and limitations observed on catalyst (promoter) control

被引：16

作者：

Kiyooka, S

Maeda, H

Abu Hena, M

Uchida, M

Kim, CS

Horiike, M

机构：

[1] Kochi Univ, Dept Chem, Kochi 7808520, Japan

[2] Kochi Univ, Dept Bioresource Sci, Nanko Ku, Kochi 7830093, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 45期

关键词：

D O I：

10.1016/S0040-4039(98)01808-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chiral oxazaborolidinone (1 and 2) -promoted asymmetric aldol reaction of pivalaldehyde with silyl nucleophile 3 resulted in excellent syn selectivity of the corresponding aldol with 96% ee. The catalyst (promoter) control was examined in the reaction with highly hindered aldehydes, 4 and 9. The reaction of 4 in the presence of 2 gave almost enantiopure aldol 7 (>50 : 1) with syn selectivity (4 : 1) in good yield. (C) 1998 Elsevier Science Ltd. All rights reserved.

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页码：8287 / 8290

页数：4

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