Iterative asymmetric synthesis of protected anti-1,3-polyols

被引：28

作者：

Enders, D ^{[1
]}

Hundertmark, T ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 22期

关键词：

asymmetric synthesis; alkylation; iteration; hydrazones;

D O I：

10.1016/S0040-4039(99)00645-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new general method for the iterative asymmetric synthesis of anti-1,3-polyol chains has been developed. The alpha,alpha'-bisalkylation of 2,2-dimethyl-1,3-dioxan-5-one SAMP-hydrazone 1 with benzyloxymethylchloride as the second electrophile leads to virtually diastereo- and enantiopure substituted 2,2-dimethyl-1,3-dioxan-5-ones with good overall yields. Their deoxygenation and conversion into primary iodides affords the electrophile for the further alkylation of 1. In this way the configurations of all new stereogenic centres are controlled by a single auxiliary. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：4169 / 4172

页数：4

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