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Citation: HAN Yu-Feng, SHEN Zong-Xuan, JIANG Hong, ZHANG Ya-Wen. Synthesis of A Chiral Catalyst for Assymetric Aldol Reaction:(4R)-Benzyloxy-(S)-proline[J]. Chinese Journal of Applied Chemistry, ;2004, 21(6): 641-643. shu

Synthesis of A Chiral Catalyst for Assymetric Aldol Reaction:(4R)-Benzyloxy-(S)-proline

1.
School of Chemistry and Chemical Engineering, Jiangsu Provincial Key Laboratory of Organic Synthesis, Suzhou University, Suzhou 215006

Corresponding author: ZHANG Ya-Wen,
Received Date: 20 August 2003
Available Online: 21 November 2003

(4R)-Hydroxy-(S)-proline was N-protected by reaction with di-tert-butyl pyrocarbonate to give N-Boc-(4R)-hydroxy-(S)-proline, which was treated with NaH in anhydrous tetrahydrofuran and followed by etherification with PhCH₂Br to form the N-Boc-(4R)-benzyloxy-(S)-proline, which, after removal of the protecting group with CF₃COOH gave the title compound. As an efficient catalyst for the direct asymmetryic aldol reaction the compound gave products in yield ranged from 58% to 77% with enantiomeric excess up to 88%.
- aldol reaction,
- chiral catalyst,
- (4R)-benzyloxy-(S)-proline,
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