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2005
Enantioselective syntheses
O 0031
Organocatalytic Kinetic Resolution of Racemic Primary Alcohols Using a Chiral
Derived from (S)-Proline. — In the presence of catalytic amounts of
31- 030 1,2-Diamine
chiral aminopyrrolidine APY and iPr2NEt, glycerol derivatives such as (I) undergo
highly selective kinetic resolutions on treatment with aromatic acyl chlorides. The
kinetic resolution of primary alcohols bearing oxiranyl, aziridinyl, tetrahydrofuryl or
tetrahydropyranyl substituents is also examined. Except for derivative (IV), only poor
to moderate selectivities are achieved. — (TERAKADO, D.; KOUTAKA, H.;
ORIYAMA*, T.; Tetrahedron: Asymmetry 16 (2005) 6, 1157-1165; Fac. Sci., Ibaraki
Univ., Mito, Ibaraki 310, Japan; Eng.) — Klein
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