Stereochemistry and Mechanism of the Ring-Opening Reaction of Cyclopropylenones with LiCu(Me)2

被引：3

作者：

Casey, Charles P. ^{[1
]}

Cesa, Mark C. ^{[2
]}

Shusterman, Alan J. ^{[3
]}

机构：

[1] Univ Wisconsin, Dept Chem, Madison, WI 53706 USA

[2] INEOS Nitriles, Naperville, IL 60563 USA

[3] Reed Coll, Dept Chem, Portland, OR 97202 USA

来源：

ORGANOMETALLICS | 2012年 / 31卷 / 22期

关键词：

ORGANOCUPRATE CONJUGATE ADDITION; ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; RAPID-INJECTION NMR; LITHIUM DIMETHYLCUPRATE; SUBSTITUTION-REACTIONS; ELECTRON-TRANSFER; COPPER(III) INTERMEDIATE; PI-COMPLEXES; CHEMISTRY; KETONES;

D O I：

10.1021/om300520r

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The chemical shifts of the diastereotopic hydrogens of the ethyl group of the cyclopropane ring-opening product of conjugate addition of LiCu(CH3)(2) to cyclopropyl enone 1 were computed. Comparison of computed and observed H-1 NMR chemical shifts of the diastereotopic hydrogens of the ethyl group of 2 established the stereochemistry of the ring-opening product as 2d-b. This provides evidence that the reaction proceeds by conjugate addition of the cuprate to the enone, followed by ring-opening of the cyclopropylmethyl copper species and reductive elimination.

引用

页码：7849 / 7854

页数：6

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