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

Research output: Contribution to journalArticle

28 Citations (Scopus)

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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Methanol
Ligands
Catalysts
Temperature
Acids
1,2,3,4-tetrahydro-1-phenylisoquinoline
aspartic acid receptor

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Enantioselective and rapid Rh-catalyzed arylation of N -tosyl- and N -nosylaldimines in methanol. / Chen, Chun Chih; Gopula, Balraj; Syu, Jin Fong; Pan, Jhih Han; Kuo, Ting Shen; Wu, Ping Yu; Henschke, Julian P.; Wu, Hsyueh-Liang.

In: Journal of Organic Chemistry, Vol. 79, No. 17, 05.09.2014, p. 8077-8085.

Research output: Contribution to journalArticle

Chen, CC, Gopula, B, Syu, JF, Pan, JH, Kuo, TS, Wu, PY, Henschke, JP & Wu, H-L 2014, 'Enantioselective and rapid Rh-catalyzed arylation of N -tosyl- and N -nosylaldimines in methanol', Journal of Organic Chemistry, vol. 79, no. 17, pp. 8077-8085. https://doi.org/10.1021/jo5012653
Chen, Chun Chih ; Gopula, Balraj ; Syu, Jin Fong ; Pan, Jhih Han ; Kuo, Ting Shen ; Wu, Ping Yu ; Henschke, Julian P. ; Wu, Hsyueh-Liang. / Enantioselective and rapid Rh-catalyzed arylation of N -tosyl- and N -nosylaldimines in methanol. In: Journal of Organic Chemistry. 2014 ; Vol. 79, No. 17. pp. 8077-8085.
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