Sulfinyl-Mediated Stereoselective Overman Rearrangements and Diels-Alder Cycloadditions

被引：5

作者：

Colomer, Ignacio ^{[1
]}

Gheewala, Chirag ^{[1
]}

Simal, Carmen ^{[1
]}

Velado, Marina ^{[1
]}

Fernandez de la Pradilla, Roberto ^{[1
]}

Viso, Alma ^{[1
]}

机构：

[1] IQOG CSIC, Inst Quim Organ Gen, Juan Cierva 3, Madrid 28006, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 10期

关键词：

BOND-FORMING HYDROGENATION; BAYLIS-HILLMAN REACTION; ENANTIOSELECTIVE ALLYLIC AMINATION; AZA-CLAISEN REARRANGEMENTS; ASYMMETRIC-SYNTHESIS; CATALYZED HYDROAMINATION; NUCLEOPHILIC EPOXIDATION; INTERMOLECULAR HYDROAMINATION; IMINE VINYLATION; HILIMAN REACTION;

D O I：

10.1021/acs.joc.6b00365

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sulfinyl trichloroacetamides are readily obtained in excellent yields through a highly stereoselective Overman rearrangement. Related bis-allylic substrates lead to amido 2-sulfinyl butadiene derivatives in excellent yields, with total chemo- and diastereoselectivity. These amido dienyl sulfoxides undergo highly selective Diels-Alder cydoadditions with N-phenylmaleimide with remarkable stereocontrol by the sulfoxide moiety.

引用

页码：4081 / 4097

页数：17

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