Stereoselective transformations of trihalomethylcarbinols induced by chromous chloride

被引：38

作者：

Bejot, R

Tisserand, S

Reddy, LM

Barma, DK

Baati, R

Falck, JR

Mioskowski, C

机构：

[1] Univ Texas, SW Med Ctr, Dept Biochem, Dallas, TX 75235 USA

[2] Univ Louis Pasteur Strasbourg 1, Fac Pharm, Lab Synth Bioortgan, UMR 7514, F-67401 Illkirch Graffenstaden, France

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 13期

关键词：

carbenes; chromium; isotopic labeling; rearrangement; synthetic methods;

D O I：

10.1002/anie.200461884

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Reduction of trihalomethylcarbinols 1 with CrCl2 affords good to excellent yields of (Z)-α-haloenol esters 2 and (Z)-β-haloenol ethers 3 through acyl or hydrogen migration, respectively. The reaction is proposed to proceed through regio- and stereoselective rearrangement of a chromium(III) Fischer carbene. (R2 = H, alkyl, aryl; X = F, Cl, Br). © 2005 Wiley-VCH Verlag GmbH S. Co. KGaA.

引用

页码：2008 / 2011

页数：4

共 25 条

[1] Chromium vinylidene carbenoids: Generation, characterization, and reactivity. First evidence for an internal proton return phenomenon with vinylidene carbenoids [J].