Enantioselective and Rapid Rh-Catalyzed Arylation of N-Tosyl- and N-Nosylaldimines in Methanol

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• 作者：Chun-Chih Chen ; Balraj Gopula ; Jin-Fong Syu ; Jhih-Han Pan ; Ting-Shen Kuo ; Ping-Yu Wu ; Julian P. Henschke ; Hsyueh-Liang Wu
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：September 5, 2014
• 年：2014
• 卷：79
• 期：17
• 页码：8077-8085
• 全文大小：358K
• ISSN：1520-6904

文摘

Enantiomerically enriched tosyl-protected diarylmethylamines were rapidly prepared by the asymmetric addition of arylboronic acids to N-tosylaldimines under mild conditions in the presence of a catalyst prepared in situ from Rh(I) and a chiral diene ligand. This methodology offers access to diarylmethylamines in good yields with excellent chiral purity at room temperature using MeOH as a solvent and NEt₃ as a base. Its synthetic utility was demonstrated by the preparation of (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline (14), an antagonist of the N-methyl-pan class="smallcaps">dpan>-aspartate (NMDA) receptor.