Catalytic Enantioselective C-C Bond-Forming Reactions of Deconjugated Butyrolactams: Michael Addition to α,β-Unsaturated Aldehydes and Ketones

被引：15

作者：

Roy, Soumya Jyoti Singha ^{[1
]}

Mukherjee, Santanu ^{[1
]}

机构：

[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 19期

关键词：

GAMMA-BUTYROLACTAM; ASYMMETRIC-SYNTHESIS; CONJUGATE ADDITIONS; BUTENOLIDES; LACTAMS; HYDROGENATION; DIVERSITY;

D O I：

10.1021/acs.joc.8b02051

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nucleophilic reactivity of deconjugated butyrolactams has been demonstrated for enantioselective Michael additions to alpha,beta-unsaturated aldehydes and ketones. These reactions are catalyzed by diphenylprolinol silyl ether and trans-1,2-diaminocyclohexane-derived bifunctional primary aminothiourea, respectively, producing the Michael adducts with moderate diastereoselectivities and good to excellent enantioselectivities (up to 99:1 er). Unlike in the case of structurally related deconjugated butenolides where vinylogous addition is prevalent, an exclusive alpha-addition is observed for deconjugated butyrolactams.

引用

页码：12071 / 12085

页数：15

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