Enantioselective and rapid Rh-catalyzed arylation of N -tosyl- and N -nosylaldimines in methanol

Chun Chih Chen, Balraj Gopula, Jin Fong Syu, Jhih Han Pan, Ting Shen Kuo, Ping Yu Wu, Julian P. Henschke, Hsyueh-Liang Wu

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Abstract

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-d-aspartate (NMDA) receptor.

Original languageEnglish
Pages (from-to)8077-8085
Number of pages9
JournalJournal of Organic Chemistry
Volume79
Issue number17
DOIs
Publication statusPublished - 2014 Sep 5

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ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Chen, C. C., Gopula, B., Syu, J. F., Pan, J. H., Kuo, T. S., Wu, P. Y., Henschke, J. P., & Wu, H-L. (2014). Enantioselective and rapid Rh-catalyzed arylation of N -tosyl- and N -nosylaldimines in methanol. Journal of Organic Chemistry, 79(17), 8077-8085. https://doi.org/10.1021/jo5012653