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.
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页码：1807 / 1816
页数：10
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