Cinchona-Diaminomethylenemalononitrile Organocatalyst for the Highly Enantioselective Hydrophosphonylation of Ketones and Enones

被引：23
作者：
Arai, Ryoga [1 ]
Hirashima, Shin-ichi [1 ]
Kondo, Junko [1 ]
Nakashima, Kosuke [1 ]
Koseki, Yuji [1 ]
Miura, Tsuyoshi [1 ]
机构：
[1] Tokyo Univ Pharm & Life Sci, 1432-1 Horinouchi, Hachioji, Tokyo 1920392, Japan
来源：
ORGANIC LETTERS | 2018年 / 20卷 / 18期
关键词：
ASYMMETRIC CONJUGATE ADDITION; ALPHA-HYDROXY PHOSPHONATES; SOLVENT-FREE CONDITIONS; CATALYTIC HYDROPHOSPHONYLATION; PHOSPHORUS NUCLEOPHILES; AL(SALALEN) COMPLEX; HERBICIDAL ACTIVITY; BIOLOGICAL-ACTIVITY; ALKYL PHOSPHONATES; CARBONYL-COMPOUNDS;
D O I：
10.1021/acs.orglett.8b02241
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The use of diaminomethylenemalononitrile (DMM) organocatalyst to promote the challenging 1,2-hydrophosphonylation of simple ketones and enones, which are also called alpha,beta-unsaturated ketones, is proposed and validated. This reaction provided the corresponding chiral alpha-hydroxy phosphonates in high to excellent yields and with enantioselectivity up to 96% ee.
引用
收藏
页码：5569 / 5572
页数：4
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