R)-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 P...R)-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 PhCH 2Br to form the N-Boc-(4R)-benzyloxy-(S)-proline, which, after removal of the protecting group with CF 3COOH 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%.展开更多
在催化剂过氧磷钨酸十二烷基吡啶盐(Cat-PW4)的作用下,α-蒎烯与H2O2反应生成主要产物(3R,4R)-4,7,7-三甲基-6-氧杂二环[3.2.1]辛烷-3,4-二醇。不同反应条件对反应转化率和选择性的实验结果表明,最佳反应条件为:12.8 mmolα-蒎烯、5 m ...在催化剂过氧磷钨酸十二烷基吡啶盐(Cat-PW4)的作用下,α-蒎烯与H2O2反应生成主要产物(3R,4R)-4,7,7-三甲基-6-氧杂二环[3.2.1]辛烷-3,4-二醇。不同反应条件对反应转化率和选择性的实验结果表明,最佳反应条件为:12.8 mmolα-蒎烯、5 m L溶剂三氯甲烷、0.2 g催化剂、3.3 m L 30%H2O2,反应温度40℃,反应时间3 h,α-蒎烯转化率和产物的选择性分别为94.7%和39.8%。反应结束后,该产物存在于水相和有机相中,通过萃取和重结晶分离提纯,得率11%,纯度达到98%;其分子结构通过红外光谱、紫外光谱、1H核磁共振谱、13C核磁共振谱、低分辨率质谱及高分辨率质谱确证。展开更多
文摘R)-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 PhCH 2Br to form the N-Boc-(4R)-benzyloxy-(S)-proline, which, after removal of the protecting group with CF 3COOH 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%.
文摘在催化剂过氧磷钨酸十二烷基吡啶盐(Cat-PW4)的作用下,α-蒎烯与H2O2反应生成主要产物(3R,4R)-4,7,7-三甲基-6-氧杂二环[3.2.1]辛烷-3,4-二醇。不同反应条件对反应转化率和选择性的实验结果表明,最佳反应条件为:12.8 mmolα-蒎烯、5 m L溶剂三氯甲烷、0.2 g催化剂、3.3 m L 30%H2O2,反应温度40℃,反应时间3 h,α-蒎烯转化率和产物的选择性分别为94.7%和39.8%。反应结束后,该产物存在于水相和有机相中,通过萃取和重结晶分离提纯,得率11%,纯度达到98%;其分子结构通过红外光谱、紫外光谱、1H核磁共振谱、13C核磁共振谱、低分辨率质谱及高分辨率质谱确证。
