N-甲氧羰基-L-3-脱氢脯氨酸甲酯与芳基重氮盐的区域和立体选择性Heck芳基化反应。神经兴奋性芳基红藻氨酸的全合成。
Regio- and stereoselective Heck arylations of N-carbomethoxy-L- 3-dehydroproline methyl ester with arenediazonium salts. Total synthesis of neuroexcitatory aryl kainoids.
作者信息
da Silva Kezia Peixoto, Godoi Marla Narciso, Correia Carlos Roque Duarte
机构信息
Instituto de Química, Universidade Estadual de Campinas, UNICAMP, C.P. 6154, 13084-971, Campinas, São Paulo, Brazil.
出版信息
Org Lett. 2007 Jul 19;9(15):2815-8. doi: 10.1021/ol070980t. Epub 2007 Jun 23.
PMID:17590003
Abstract
The Heck arylation of N-carbomethoxy-L-3-dehydroproline methyl ester with arenediazonium tetrafluoroborates produced chiral 4-aryldehydroproline derivatives in moderate to good yields in a highly regio- and stereocontrolled fashion. A rationale for the unexpected high regioselectivity is provided using Deeth's model. Heck adduct 15 (G = o-CH3O) was converted into several aryl kainoids using concise and efficient routes.
摘要
N-甲氧羰基-L-3-脱氢脯氨酸甲酯与四氟硼酸芳基重氮盐的Heck芳基化反应以高度区域和立体控制的方式，以中等至良好的产率生成了手性4-芳基脱氢脯氨酸衍生物。使用迪思模型对意外的高区域选择性给出了一种解释。通过简洁有效的路线将Heck加合物15（G = 邻甲氧基）转化为几种芳基红藻氨酸类似物。
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