| 光学活性姜黄烯化合物的立体选择性合成 |
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| 引用本文： | 王智贤,陈钟瑛.光学活性姜黄烯化合物的立体选择性合成[J].有机化学,1993,13(3):244-249. |
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| 作者姓名： | 王智贤 陈钟瑛 |
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| 作者单位： | 华东化工学院化学制药研究室 上海(王智贤)，华东化工学院化学制药研究室 200237(陈钟瑛) |
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| 摘 要： | 本文报道了在手性膦过渡金属配合物催化下,以对溴甲苯与6-甲基-5-庚烯-2-溴化镁(5)经不对称交叉偶联反应合成(R)-(-)-和(S)-(+_)-α-姜黄烯的方法,光学收率分别为44%e.e和50.3%e.e.(R)-(-)-α-姜黄烯经Birch还原得到(R)-(-)-β-姜黄烯.对溴苯甲醚经不对称交叉偶联、Birch还原等反应合成了(S)-(+)-γ-姜黄烯.
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| 关 键 词： | 倍半萜 催化剂 苯 P 溴代烃 膦 过渡金属络合物 手征性 庚烯 P 格氏试剂 精油 |
Stereoselective synthesis of optically active curcumenes |
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| WANG Zhi-Xian,CHENG Zhong-Yin Laboratory of Pharmaceutics,East China University of Chemical Technology,Shanghai.Stereoselective synthesis of optically active curcumenes[J].Chinese Journal of Organic Chemistry,1993,13(3):244-249. |
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| Authors: | WANG Zhi-Xian CHENG Zhong-Yin Laboratory of Pharmaceutics East China University of Chemical Technology Shanghai |
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| Institution: | WANG Zhi-Xian,CHENG Zhong-Yin Laboratory of Pharmaceutics,East China University of Chemical Technology,Shanghai,200237 |
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| Abstract: | A new and feasible method for synthesizing optically active (R)- and (S)-(+)-a-curcumene (I) via 6-methyl-5-hepten-2-ylmagnesium bromide asym. cross-coupling reaction with p-bromotoluene catalyzed by chiral phosphine-transition metal complexes, in optical yield up to 50% e.e., was described. (R)-(-)-a-Curcumene was converted into (R)-(-)-b-curcumene (II) by Birch reduction (S)-(+)-g-Curcumene (III) was synthesized from p-bromophenylmethyl ether via asym. cross-coupling, Birch reduction etc. |
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| Keywords: | asymmetric cross-coupling stereoselective synthesis sesquiterpene optically active curcumenes |
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