ASYMMETRIC MICHAEL ADDITIONS VIA SAMP-/RAMP-HYDRAZONES ENANTIOSELECTIVE SYNTHESIS OF 2-SUBSTITUTED 4-OXOSULFONES

被引：19

作者：

ENDERS, D ^{[1
]}

PAPADOPOULOS, K ^{[1
]}

HERDTWECK, E ^{[1
]}

机构：

[1] TECH UNIV GARCHING,INST ANORGAN CHEM,W-8046 GARCHING,GERMANY

来源：

TETRAHEDRON | 1993年 / 49卷 / 09期

关键词：

D O I：

10.1016/S0040-4020(01)80538-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and efficient enantioselective synthesis of 2-substituted 4-oxosulfones 5 in 40 - 71% overall chemical yield and enantiomeric excesses of 86->97% is described. The key step is an asymmetric Michael-addition of lithiated methylketone -SAMP-/RAMP-hydrazones 3 to alpha,beta-unsaturated phenylsulfones 2. The absolute configuration is determined by X-ray structure analysis of a crystalline hydrazone Michael adduct (4k) and through chemical correlation by polarimetry.

引用

页码：1821 / 1830

页数：10

共 37 条

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