Journal of Organic Chemistry p. 8077 - 8085 (2014)
Update date:2022-08-03
Topics:
Chen, Chun-Chih
Gopula, Balraj
Syu, Jin-Fong
Pan, Jhih-Han
Kuo, Ting-Shen
Wu, Ping-Yu
Henschke, Julian P.
Wu, Hsyueh-Liang
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.
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