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Lipase catalyzed transesterification of 2‐substituted 3‐hydroxy esters
Author(s) -
Kaga Harumi,
Hirosawa Kunio,
Takahashi Tomiki,
Goto Kouhei
Publication year - 1998
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/(sici)1520-636x(1998)10:7<693::aid-chir15>3.0.co;2-v
Subject(s) - chemistry , transesterification , kinetic resolution , lipase , stereocenter , vinyl acetate , catalysis , chirality (physics) , organic chemistry , resolution (logic) , acyl group , stereochemistry , group (periodic table) , enantioselective synthesis , enzyme , copolymer , polymer , chiral symmetry breaking , physics , quantum mechanics , artificial intelligence , quark , computer science , nambu–jona lasinio model
Kinetic resolution of 2‐substituted 3‐hydroxy esters was examined by lipase PS catalyzed transesterification using vinyl acetate as an acyl donor. Resolution of (±)‐ syn ‐ and ‐ anti ‐1a, ‐1e possessing a small methyl group at the C‐3 position was accomplished enantioselectively. The outcome of the resolution seems to be related to the differences in size of the substituents at the stereocenter bearing a secondary hydroxy group. Chirality 10:693–698, 1998. © 1998 Wiley‐Liss, Inc.