基于脯氨酸磺酰胺的有机催化：迟做总比不做好。
Proline Sulfonamide-Based Organocatalysis: Better Late than Never.
作者信息
Yang Hua, Carter Rich G
机构信息
Department of Chemistry, Oregon State University, Corvallis, OR 97331.
出版信息
Synlett. 2010 Sep 1;2010(19):2827-2838. doi: 10.1055/s-0030-1259020.
Abstract
The history of proline sulfonamides for use in catalyzing highly enantioselective and diastereoselective C-C bond forming reactions is described. Highlighted is the development of N-(p-dodecylphenylsulfonyl)-2-pyrrolidinecarboxamide ("Hua Cat") and N-(carboxy-p-dodecylphenylsulfonyl)-2-pyrrolidinecarboxamide ("Hua Cat-II") by Yang and Carter. Specific reactions covered include the aldol reaction, Mannich reaction, formal aza-Diels-Alder reaction, tandem Michael/Mannich reaction and Yamada-Otani reaction. The ability of proline aryl sulfonamides to construct all-carbon quaternary stereocenters in high enantioselectivity and diastereoselectivity is a notable feature of the reported work. The practicality of this chemistry for large scale and industrial applications is also included. Finally, a discussion of the future directions of proline sulfonamide organocatalysis is provided.
摘要
本文描述了脯氨酸磺酰胺用于催化高对映选择性和非对映选择性碳-碳键形成反应的历史。重点介绍了Yang和Carter开发的N-（对十二烷基苯磺酰基）-2-吡咯烷甲酰胺（“华催化剂”）和N-（羧基-对十二烷基苯磺酰基）-2-吡咯烷甲酰胺（“华催化剂-II”）。所涵盖的具体反应包括羟醛反应、曼尼希反应、形式上的氮杂狄尔斯-阿尔德反应、串联迈克尔/曼尼希反应和山田-大谷反应。脯氨酸芳基磺酰胺以高对映选择性和非对映选择性构建全碳季碳立体中心的能力是所报道工作的一个显著特征。还包括这种化学方法在大规模和工业应用中的实用性。最后，对脯氨酸磺酰胺有机催化的未来发展方向进行了讨论。
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