Chemoenzymatic Synthesis of (2 S )‐ and (2 R )‐2‐(1,3‐Dithian‐2‐ylmethyl)oxirane | Zendy

Sundby Eirik | Zendy; Holt Jarle | Zendy; Vik Anders | Zendy; Anthonsen Thorleif | Zendy

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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)

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