Asymmetric synthesis of α,γ-substituted γ-sultones via allylation of chiral lithiated Sulfonates

被引：17

作者：

Enders, D ^{[1
]}

Harnying, W ^{[1
]}

Vignola, N ^{[1
]}

机构：

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

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 2003卷 / 20期

关键词：

sultones; asymmetric synthesis; chiral auxiliaries; sulfonates; one-pot reaction; cyclization;

D O I：

10.1002/ejoc.200300342

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first auxiliary controlled asymmetric synthesis of enantiopure alpha,gamma-substituted (gamma-sultones via alpha-allylation of lithiated sulfonates by using 1,2:5,6-di-O-isopropylidene-alpha-D-allofuranose as chiral auxiliary is described. The high asymmetric inductions of the alpha-allylations were reached in good to excellent yields. Successive epimerization-free cleavage of the auxiliary and diastereoselective ring closure of the sulfonic acid intermediates in a one-pot procedure led to the title compounds in good to excellent yields and diastereo- and enantiomeric excesses (de, ee greater than or equal to 98%). ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).

引用

页码：3939 / 3947

页数：9

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