Dynamic kinetic resolution of racemic beta-haloalcohols: direct access to enantioenriched epoxides.
The direct chemo-enzymatic DKR of racemic beta-haloalcohols is reported, yielding the corresponding optically active epoxides in a single step. The mutant haloalcohol dehalogenase HheC Cys153Ser Trp249Phe is used for the asymmetric ring closure, whereas racemization of the remaining enantiomer of the haloalcohol is achieved using the new iridacycle 3, one of the most effective racemization catalysts to date for beta-haloalcohols.
Haak
Robert M
RM
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.
Berthiol
Florian
F
Jerphagnon
Thomas
T
Gayet
Arnaud J A
AJ
Tarabiono
Chiara
C
Postema
Christiaan P
CP
Ritleng
Vincent
V
Pfeffer
Michel
M
Janssen
Dick B
DB
Minnaard
Adriaan J
AJ
Feringa
Ben L
BL
de Vries
Johannes G
JG
D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D004852:Epoxy Compounds / Q000737:chemistry*; D006219:Halogens / Q000737:chemistry*; D007700:Kinetics; D015394:Molecular Structure; D013237:Stereoisomerism
D000438:Alcohols; D004852:Epoxy Compounds; D006219:Halogens