Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 17, Pages 8077-8085Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo5012653
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- Ministry of Science and Technology of Republic of China [100-2113-M-003-009-MY2, 102-2113-M-003-006-MY2]
- National Taiwan Normal University
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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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