(1R,2R)-(−)-2-Dimethylamino-1-(4-nitrophenyl)-1,3- propanediol/l-proline cocatalyzed enantioselective Morita–Baylis–Hillman reaction
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- 作者：Hongying Tang ; Peng Gao ; Guofeng Zhao ; Zhenghong Zhou ; Liangnian He ; Chuchi Tang
- 关键词：(1R ; 2R)-(− ; )-2-Dimethylamino-1-(4-nitrophenyl)-1 ; 3-propanediol ; Cocatalyst ; Asymmetric Morita– ; Baylis– ; Hillman reaction ; Enantioselectivity
- 刊名：Catalysis Communications
- 出版年：2007
- 出版时间：November 2007
- 年：2007
- 卷：8
- 期：11
- 页码：1811-1814
- 全文大小：122 K
文摘
(1R,2R)-(−)-2-Dimethylamino-1-(4-nitrophenyl)-1,3-propanediol (2) was prepared starting from the readily available precursor of antibiotics chloramphenicol. The combination of compound 2 and l-proline have been found to be an efficient cocatalyst for the asymmetric Morita–Baylis–Hillman (MBH) reaction between methyl vinyl ketone (MVK) and aromatic aldehydes. The corresponding adducts were formed in reasonable chemical yields with good enantioselectivities (up to 82 % ee). Performance of parallel cocatalytic reactions with chiral amine 2 and the two enantiomers of proline revealed that it is the proline stereochemistry that determines the configuration of the newly formed chiral center.