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Stereoselective Transformations of Trihalomethylcarbinols Induced by Chromous Chloride
Author(s) -
Bejot Romain,
Tisserand Steve,
Reddy L. Manmohan,
Barma Deb K.,
Baati Rachid,
Falck J. R.,
Mioskowski Charles
Publication year - 2005
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200461884
Subject(s) - stereoselectivity , carbene , chromium , alkyl , chemistry , aryl , reduction (mathematics) , chloride , medicinal chemistry , organic chemistry , combinatorial chemistry , catalysis , mathematics , geometry
Reduction of trihalomethylcarbinols 1 with CrCl 2 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. (R 2 =H, alkyl, aryl; X=F, Cl, Br).