A novel chiral synthetic equivalent of glyoxal and its application to the asymmetric synthesis of O-protected α-hydroxy aldehydes

被引：16

作者：

Colombo, L ^{[1
]}

Di Giacomo, M ^{[1
]}

机构：

[1] Univ Pavia, Dipartimento Chim Farmaceut, I-27100 Pavia, Italy

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 10期

关键词：

D O I：

10.1016/S0040-4039(99)00095-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diastereomerically pure 2-formyl-N-Boc-1,3-oxazolidine 7 was prepared in 83% yield from stannyloxazolidine 4, Grignard additions to the formyl group of compound 7 in the presence of Lewis acids afforded diastereomerically pure secondary carbinols 8. Protection of the hydroxyl group and unmasking of the oxazolidine ring gave O-protected alpha-hydroxy aldehydes 11, which were immediately reduced to the corresponding 1,2-diols 12, (C) 1999 Elsevier Science Ltd. All rights reserved.

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页码：1977 / 1980

页数：4

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