Enantiocomplementary Chemoenzymatic Asymmetric Synthesis of ( R )‐ and ( S )‐Chromanemethanol | Zendy

Fuchs Michael | Zendy; Simeo Yolanda | Zendy; Ueberbacher Barbara T. | Zendy; Mautner Barbara | Zendy; Netscher Thomas | Zendy; Faber Kurt | Zendy

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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)

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