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Chemoenzymatic Synthesis of (2 S )‐ and (2 R )‐2‐(1,3‐Dithian‐2‐ylmethyl)oxirane
Author(s) -
Sundby Eirik,
Holt Jarle,
Vik Anders,
Anthonsen Thorleif
Publication year - 2004
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.200300320
Subject(s) - chemistry , enantiomer , epoxide , lipase , propanol , stereochemistry , enzyme , organic chemistry , medicinal chemistry , catalysis , ethanol
Lipase‐catalyzed transesterifications and biological reductions were used to obtain the ( S )‐enantiomers of 3‐chloro‐1‐(1,3‐dithian‐2‐yl)‐2‐propanol and 1‐(1,3‐dithian‐2‐yl)‐3‐fluoro‐2‐propanol and their ( R )‐acetates. ( S )‐3‐Chloro‐1‐(1,3‐dithian‐2‐yl)‐2‐propanol and ( R )‐3‐chloro‐1‐(1,3‐dithian‐2‐yl)‐2‐propyl acetate were converted into the respective enantiomers of 2‐(1,3‐dithian‐2‐ylmethyl)oxirane. During this work we also isolated a new gem ‐disubstituted epoxide, 2‐(chloromethyl)‐2‐(1,3‐dithian‐2‐yl)oxirane. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)