Ba-Catalyzed Direct Mannich-Type Reactions of a β,γ-Unsaturated Ester Providing β-Methyl aza-Morita−Baylis−Hillman-Type Products
Ba-Catalyzed Direct Mannich-Type Reactions of a β,γ-Unsaturated Ester Providing β-Methyl aza-Morita−Baylis−Hillman-Type Products
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DOI：
10.1021/ol071380x
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发表时间：
2007-07
期刊：
影响因子：
5.2
通讯作者：
A. Yamaguchi;Naohiro Aoyama;S. Matsunaga;M. Shibasaki
中科院分区：
文献类型：
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作者：
A. Yamaguchi;Naohiro Aoyama;S. Matsunaga;M. Shibasaki
介绍了钡催化的β，γ-不饱和酯的直接Mannich型反应。Ba催化剂不仅促进了曼尼希型反应，而且异构化了曼尼希加合物，从各种芳基、杂芳基和烷基亚胺以61 - 88%的产率得到β-甲基氮杂-森田−贝利斯−希尔曼型产物。初步试验的对映体选择性的变体与手性联芳基二醇配体得到的产品在高达80%ee。
Barium-catalyzed direct Mannich-type reactions of a β,γ-unsaturated ester are described. The Ba-catalyst not only promoted the Mannich-type reactions, but also isomerized Mannich adducts to afford β-methyl aza-Morita−Baylis−Hillman-type products in 61−88% yield from various aryl, heteroaryl, and alkyl imines. Preliminary trials on enantioselective variants with a chiral biaryldiol ligand gave products in up to 80% ee.