Stereoselective transformations of trihalomethylcarbinols induced by chromous chloride

Romain Bejot; Steve Tisserand; L. Manmohan Ready; Deb K. Barma; Rachid Baati; J. R. Falck; Charles Mioskowski

doi:10.1002/anie.200461884

Stereoselective transformations of trihalomethylcarbinols induced by chromous chloride

Romain Bejot, Steve Tisserand, L. Manmohan Ready, Deb K. Barma, Rachid Baati, J. R. Falck, Charles Mioskowski

Biochemistry

Research output: Contribution to journal › Article › peer-review

36 Scopus citations

Abstract

(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).

Original language	English (US)
Pages (from-to)	2008-2011
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	44
Issue number	13
DOIs	https://doi.org/10.1002/anie.200461884
State	Published - Mar 18 2005

Keywords

Carbenes
Chromium
Isotopic labeling
Rearrangement
Synthetic methods

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.200461884

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title = "Stereoselective transformations of trihalomethylcarbinols induced by chromous chloride",

abstract = "(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).",

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author = "Romain Bejot and Steve Tisserand and Ready, {L. Manmohan} and Barma, {Deb K.} and Rachid Baati and Falck, {J. R.} and Charles Mioskowski",

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doi = "10.1002/anie.200461884",

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T1 - Stereoselective transformations of trihalomethylcarbinols induced by chromous chloride

AU - Bejot, Romain

AU - Tisserand, Steve

AU - Ready, L. Manmohan

AU - Barma, Deb K.

AU - Baati, Rachid

AU - Falck, J. R.

AU - Mioskowski, Charles

PY - 2005/3/18

Y1 - 2005/3/18

N2 - (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).

AB - (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).

KW - Carbenes

KW - Chromium

KW - Isotopic labeling

KW - Rearrangement

KW - Synthetic methods

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VL - 44

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EP - 2011

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 13

ER -

Stereoselective transformations of trihalomethylcarbinols induced by chromous chloride

Abstract

Keywords

ASJC Scopus subject areas

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