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*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

45 Citations (Scopus)


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
Issue number17
Publication statusPublished - 2014 Sept 5

ASJC Scopus subject areas

  • Organic Chemistry


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