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Enantiocomplementary Chemoenzymatic Asymmetric Synthesis of ( R )‐ and ( S )‐Chromanemethanol
Author(s) -
Fuchs Michael,
Simeo Yolanda,
Ueberbacher Barbara T.,
Mautner Barbara,
Netscher Thomas,
Faber Kurt
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800950
Subject(s) - enantiopure drug , chemistry , epoxide hydrolase , kinetic resolution , chirality (physics) , stereochemistry , lipase , enantioselective synthesis , total synthesis , epoxide , organic chemistry , enzyme , catalysis , microsome , chiral symmetry breaking , physics , quantum mechanics , quark , nambu–jona lasinio model
A non‐lipase‐based, enantiocomplementary chemoenzymatic route towards enantiopure ( R )‐ and ( S )‐chromanemethanol ( 12 ), which are the key building blocks for the synthesis of stereoisomerically pure α‐tocopherols, has been achieved by the biocatalytic resolution of a racemic 2,2‐disubstituted oxirane using an epoxide hydrolase and a halohydrin dehalogenase, which exhibit opposite enantiopreferences. The introduction of chirality at an early stage of the synthesis ensured a high efficiency, leading to total overall yields of 16 and 26 % for ( R )‐ and ( S )‐chromanemethanol ( 12 ), respectively.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)