Stereoselective reaction of 2-carboxythioesters-1,3-dithiane with nitroalkenes: an organocatalytic strategy for the asymmetric addition of a glyoxylate anion equivalent

被引：22

作者：

Massolo, Elisabetta ^{[1
]}

Benaglia, Maurizio ^{[1
]}

Genoni, Andrea ^{[1
]}

Annunziata, Rita ^{[1
]}

Celentano, Giuseppe ^{[2
]}

Gaggero, Nicoletta ^{[2
]}

机构：

[1] Univ Milan, Dipartimento Chim, I-20133 Milan, Italy

[2] Univ Milan, Dipartimento Sci Farmaceut, I-20133 Milan, Italy

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 20期

关键词：

CATALYTIC CONJUGATE ADDITION; TERT-BUTYL HYDRAZONE; ALPHA-KETO ESTERS; ACYL ANION; ALPHA; BETA-UNSATURATED ALDEHYDES; MICHAEL REACTION; BIFUNCTIONAL ORGANOCATALYSTS; ENANTIOSELECTIVE SYNTHESIS; TRIFLUOROETHYL THIOESTERS; DUAL ACTIVATION;

D O I：

10.1039/c5ob00492f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient organocatalytic methodology has been developed to perform the stereoselective addition of 2-carboxythioesters-1,3-dithiane to nitroalkenes. Under mild reaction conditions gamma-nitro-beta-aryl-alpha-keto esters with up to 92% ee were obtained, realizing a formal catalytic stereoselective conjugate addition of the glyoxylate anion synthon. The reaction products are versatile starting materials for further synthetic transformations; for example, the simultaneous reduction of the nitro group and removal of the dithiane ring was accomplished, allowing the preparation of a GABA(B) receptor agonist baclofen.

引用

页码：5591 / 5596

页数：6

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