Desymmetrization of acid anhydride with asymmetric esterification catalyzed by chiral phosphoric acid

被引：20
|
作者：
Yamada, Ken-ichi [1 ,2 ]
Oonishi, Akinori [1 ]
Kuroda, Yusuke [1 ]
Harada, Shingo [1 ]
Kiyama, Hiroki [1 ]
Yamaoka, Yousuke [1 ]
Takasu, Kiyosei [1 ]
机构：
[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
[2] Univ Tokushima, Grad Sch Pharmaceut Sci, Shomachi, Tokushima 7708505, Japan
来源：
TETRAHEDRON LETTERS | 2016年 / 57卷 / 36期
关键词：
Organocatalysis; Desymmetrization; Acid anhydride; Chiral phosphoric acid; Chiral Bronsted acid; PIG-LIVER ESTERASE; STRONGER BRONSTED ACIDS; CYCLIC ANHYDRIDES; ENANTIOSELECTIVE DESYMMETRIZATION; ORGANOCATALYTIC DESYMMETRIZATION; GLUTARIC ANHYDRIDES; SECONDARY ALCOHOLS; ORGANIC-SYNTHESIS; LACTONE SYNTHONS; MESO-ANHYDRIDES;
D O I：
10.1016/j.tetlet.2016.07.093
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Asymmetric desymmetrization of sigma-symmetric acid anhydrides was achieved with chiral phosphoric acid as a Bronsted acid catalyst. The key of success was finding of benzhydrol and 2,2-diphenylethanol as the nucleophiles of choice. The corresponding half esters were obtained in good yields with high selectivity. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4098 / 4100
页数：3
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