TY - JOUR
T1 - Lipase-catalyzed dynamic kinetic resolution giving optically active cyanohydrins
T2 - use of silica-supported ammonium hydroxide and porous ceramic-immobilized lipase
AU - Sakai, Takashi
AU - Wang, Kefei
AU - Ema, Tadashi
N1 - Copyright:
Copyright 2008 Elsevier B.V., All rights reserved.
PY - 2008/2/25
Y1 - 2008/2/25
N2 - Synthetically useful cyanohydrin acetates, ArCH(OAc)CN (Ar=C6H5, 3,4-methylenedioxyphenyl, 4-Me-C6H4, 4-Cl-C6H4, 4-F-C6H4, 4-CF3-C6H4), were successfully synthesized in high enantiomeric purities (79-93% ee) via the lipase-catalyzed dynamic kinetic resolution (DKR) of cyanohydrins synthesized in situ from the corresponding aldehydes and acetone cyanohydrin. The combined use of silica-supported BTAH (benzyltrimethylammonium hydroxide) and porous ceramic-immobilized lipase under the optimized reaction conditions enabled the remarkable acceleration of the enantioselective DKR reactions.
AB - Synthetically useful cyanohydrin acetates, ArCH(OAc)CN (Ar=C6H5, 3,4-methylenedioxyphenyl, 4-Me-C6H4, 4-Cl-C6H4, 4-F-C6H4, 4-CF3-C6H4), were successfully synthesized in high enantiomeric purities (79-93% ee) via the lipase-catalyzed dynamic kinetic resolution (DKR) of cyanohydrins synthesized in situ from the corresponding aldehydes and acetone cyanohydrin. The combined use of silica-supported BTAH (benzyltrimethylammonium hydroxide) and porous ceramic-immobilized lipase under the optimized reaction conditions enabled the remarkable acceleration of the enantioselective DKR reactions.
KW - Cyanohydrin
KW - Dynamic kinetic resolution
KW - Lipase
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U2 - 10.1016/j.tet.2007.12.030
DO - 10.1016/j.tet.2007.12.030
M3 - Article
AN - SCOPUS:38349163135
SN - 0040-4020
VL - 64
SP - 2178
EP - 2183
JO - Tetrahedron
JF - Tetrahedron
IS - 9
ER -