引用本文:
韩玉峰, 沈宗旋, 蒋虹, 张雅文. 手性催化剂(4R)-苄氧基-(S)-脯氨酸的合成及其对不对称羟醛反应的催化活性[J]. 应用化学,
2004, 21(6): 641-643.
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.
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.
手性催化剂(4R)-苄氧基-(S)-脯氨酸的合成及其对不对称羟醛反应的催化活性
摘要:
2000年,List等[1]以丙酮和对硝基苯甲醛为模型报道了第一例脯氨酸催化的不对称直接羟醛反应(Direct asymmetric aldol reaction)。
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关键词:
- 羟醛反应
- / 手性催化剂
- / (4R)-苄氧基-(S)-脯氨酸
- / 合成
English
Synthesis of A Chiral Catalyst for Assymetric Aldol Reaction:(4R)-Benzyloxy-(S)-proline
Abstract:
(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%.
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Key words:
- aldol reaction
- / chiral catalyst
- / (4R)-benzyloxy-(S)-proline
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