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2005
Oxazole derivatives
R 0220
Highly Enantioselective Synthesis of (R)-α-Alkylserines via Phase-Transfer
Alkylation of o-Biphenyl-2-oxazoline-4-carboxylic Acid tert-Butyl Ester
37- 127 Catalytic
Using Cinchona-Derived Catalysts. — Oxazolines (III) are prepared by the title
method as precursors for (R)-α-alkylserines. Among 9 substrates examined, o-biphenyl
derivative (I) affords the highest enantioselectivity in the reaction with benzyl bromide
by use of cinchona-derived catalyst ACB. Under optimized conditions concerning base
and reaction temperature, the alkylation of (I) with bromides (II) gives up to 96% enantioselectivity. — (LEE, Y.-J.; LEE, J.; KIM, M.-J.; KIM, T.-S.; PARK*, H.-G.; JEW,
S.-S.; Org. Lett. 7 (2005) 8, 1557-1560; Coll. Pharm., Seoul Natl. Univ., Kwanak,
Seoul 151-742, S. Korea; Eng.) — Klein
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