Asymmetric synthesis of cis-3,4-disubstituted β-sultams

被引：16

作者：

Enders, D ^{[1
]}

Moll, A ^{[1
]}

机构：

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

来源：

SYNTHESIS-STUTTGART | 2005年 / 11期

关键词：

asymmetric synthesis; reductive cleavage; 1,2-aminothiol; ring-closure; 1,2-thiazetidine 1,1-dioxides;

D O I：

10.1055/s-2005-865326

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric synthesis of cis-3,4-disubstituted beta-sultams is reported. The protocol is based on the oxidation of 1,2-aminothiols with H2O2 and ammonium heptamolybdate. The chlorination of the resulting beta-amino sulfonic acids was achieved utilising a solution of phosgene in toluene. The beta-aminosulfonyl chlorides obtained were cyclised to the title compounds under basic conditions without epimerisation (de, ee >= 96%) and good overall yields (17-59%). In addition, the N-Cbz-protection of beta-sultams was easily accomplished.

引用

页码：1807 / 1816

页数：10

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