Efficient general asymmetric syntheses of 3-substituted 1(3H)-isobenzofuranones in very high enantiomeric excess

被引：71

作者：

Ramachandran, PV ^{[1
]}

Chen, GM ^{[1
]}

Brown, HC ^{[1
]}

机构：

[1] PURDUE UNIV, HC BROWN & RB WETHERILL LABS CHEM, W LAFAYETTE, IN 47907 USA

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 13期

关键词：

D O I：

10.1016/0040-4039(96)00260-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The intermolecular asymmetric reduction of methyl o-(1-oxoalkyl)benzoates with B-chlorodiisopinocampheylborane provides, after workup, 3-alkylphthalides in greater than or equal to 97% ee. Unfortunately, this procedure is not as efficient for the preparation of 3-arylphthalides. However, an intramolecular reduction of B-(o-benzoylbenzoyloxy)diisopinocampheylborane readily prepared by the treatment of o-benzoyl benzoic acid with diisopinocampheylborane, provides 3-phenylphthalide in greater than or equal to 96% ee.

引用

页码：2205 / 2208

页数：4

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