Facile synthesis of chiral 1,2-chlorohydrins via the ring-opening of meso-epoxides catalyzed by chiral phosphine oxides

被引：21

作者：

Kotani, Shunsuke ^{[1
]}

Furusho, Haruka ^{[2
]}

Sugiura, Masaharu ^{[2
]}

Nakajima, Makoto ^{[2
]}

机构：

[1] Kumamoto Univ, Prior Org Innovat & Excellence, Kumamoto, Japan

[2] Kumamoto Univ, Grad Sch Pharmaceut Sci, Kumamoto, Japan

来源：

TETRAHEDRON | 2013年 / 69卷 / 14期

关键词：

Chlorohydrin; meso-Epoxide; Enantioselective; Halogenation; Lewis base; PYRIDINE N-OXIDES; LEWIS-BASE; STEREOSELECTIVE REACTIONS; SILICON TETRACHLORIDE; ASYMMETRIC CATALYSIS; CLEAVAGE; FLUORIDE; FAMILY;

D O I：

10.1016/j.tet.2013.01.066

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The facile synthesis of chiral 1,2-chlorohydrins via the enantioselective ring-opening of meso-epoxides with silicon tetrachloride in the presence of a chiral phosphine oxide was accomplished. The chiral 1,2-chlorohydrins were also obtained from the corresponding cis-alkenes in one-pot without significant loss in the selectivity, thereby permitting easy access to the 1,2-chlorohydrins from cis-alkenes with good yields and enantioselectivities. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：3075 / 3081

页数：7

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