Regio- and Stereoselective Heck Arylations of N-Carbomethoxy-L- 3-Dehydroproline Methyl Ester with Arenediazonium Salts. Total Synthesis of Neuroexcitatory Aryl Kainoids

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• 作者：Kezia Peixoto da Silva ; Marla Narciso Godoi ; Carlos Roque Duarte Correia
• 刊名：Organic Letters
• 出版年：2007
• 出版时间：July 19, 2007
• 年：2007
• 卷：9
• 期：15
• 页码：2815 - 2818
• 全文大小：93K
• 年卷期：v.9,no.15(July 19, 2007)
• ISSN：1523-7052

文摘

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 highregioselectivity is provided using Deeth's model. Heck adduct 15 (G = o-CH₃O) was converted into several aryl kainoids using concise andefficient routes.