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Chemoenzymatic Synthesis of (2S)- and (2R)-2-(1,3-Dithian-2-ylmethyl)oxirane

✍ Scribed by Eirik Sundby; Jarle Holt; Anders Vik; Thorleif Anthonsen

Publisher
John Wiley and Sons
Year
2004
Tongue
English
Weight
106 KB
Volume
2004
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

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)

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