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

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posted on 05.09.2014, 00:00 by Chun-Chih Chen, Balraj Gopula, Jin-Fong Syu, Jhih-Han Pan, Ting-Shen Kuo, Ping-Yu Wu, Julian P. Henschke, Hsyueh-Liang Wu
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.