Asymmetric Conjugate Addition of Phosphonates to Enones Using Cinchona-Diaminomethylenemalononitrile Organocatalysts

被引：35

作者：

Arai, Ryoga ^{[1
]}

Hirashima, Shin-ichi ^{[1
]}

Nakano, Tatsuki ^{[1
]}

Kawada, Masahiro ^{[1
]}

Akutsu, Hiroshi ^{[1
]}

Nakashima, Kosuke ^{[1
]}

Miura, Tsuyoshi ^{[1
]}

机构：

[1] Tokyo Univ Pharm & Life Sci, Hachioji, Tokyo 1920392, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 05期

基金：

日本学术振兴会;

关键词：

ENANTIOSELECTIVE MICHAEL ADDITION; DIPHENYL PHOSPHITE; DIETHYL PHOSPHITE; SQUARAMIDE; HYDROPHOSPHONYLATION; NITROOLEFINS; NITROALKENES; ALDEHYDES; LIGANDS;

D O I：

10.1021/acs.joc.9b02553

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric conjugate additions of phosphonates to trans-crotonophenone and chalcone derivatives using a diamino-methylenemalononitrile organocatalyst resulted in the generation of the corresponding chiral gamma-ketophosphonates in high yields with excellent enantioselectivities (up to 95% ee). This report is the first successful example of asymmetric 1,4-additions of phosphonate to alpha,beta-unsaturated ketones using an organocatalyst.

引用

页码：3872 / 3878

页数：7

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