Synthesis of enantiopure chloroalcohols by enzymatic kinetic resolution.
3-Alkenyl and heteroaryl chloroalcohols have been obtained in excellent enantiomeric excess (>99%) by enzymatic kinetic resolution using the haloalcohol dehalogenase HheC. Yields were close to the theoretical maximum for all substrates employed. Furthermore, the applicability of this methodology on multigram scale has been established.
Haak
Robert M
RM
Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands.
Tarabiono
Chiara
C
Janssen
Dick B
DB
Minnaard
Adriaan J
AJ
de Vries
Johannes G
JG
Feringa
Ben L
BL
D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D002713:Chlorine / Q000737:chemistry*; D002855:Chromatography, Thin Layer; D006867:Hydrolases / Q000737:chemistry; D006868:Hydrolysis; D007700:Kinetics; D008956:Models, Chemical; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism; D013696:Temperature
D000438:Alcohols; D002713:Chlorine; D006867:Hydrolases; C113022:haloalcohol dehalogenase