Efficient syntheses of four stable-isotope labeled (1R)-menthyl (1S,2S)-(+)-2-phenylcyclopropanecarboxylates

被引：10

作者：

Keliher, Edmund J. ^{[1
]}

Burrell, Richard C. ^{[1
]}

Chobanian, Harry R. ^{[1
]}

Conkrite, Karina L. ^{[1
]}

Shukla, Rajesh ^{[1
]}

Baldwin, John E. ^{[1
]}

机构：

[1] Syracuse Univ, Dept Chem, Syracuse, NY 13244 USA

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2006年 / 4卷 / 14期

关键词：

D O I：

10.1039/b605912k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Many carbenoid cyclopropanation reactions promoted by chiral catalysts give product mixtures reflecting impressive diastereo- and enantioselectivities. Few provide a single chiral product efficiently. This limitation has been overcome in cyclopropanations of styrene and isotopically labeled styrenes with alpha-diazoacetates. Convenient syntheses on a 20 g scale of each of four chiral isotopically labeled (1R)-menthyl(1S, 2S)-2-phenylcyclopropanecarboxylates ( the 1-d- 3-C-13,1,(3S)-d(2), 1,2,( 3S)-d(3), and 1,3,3-d(3) isotopomers) of better than 99% ee have been realized.

引用

页码：2777 / 2784

页数：8

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