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

doi:10.1021/jo5012653

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 journal › Article › peer-review

45 Scopus citations

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 language	English
Pages (from-to)	8077-8085
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	79
Issue number	17
DOIs	https://doi.org/10.1021/jo5012653
State	Published - 5 Sep 2014
Externally published	Yes

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title = "Enantioselective and rapid Rh-catalyzed arylation of N -tosyl- and N -nosylaldimines in methanol",

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.",

author = "Chen, {Chun Chih} and Balraj Gopula and Syu, {Jin Fong} and Pan, {Jhih Han} and Kuo, {Ting Shen} and Wu, {Ping Yu} and Henschke, {Julian P.} and Wu, {Hsyueh Liang}",

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doi = "10.1021/jo5012653",

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T1 - Enantioselective and rapid Rh-catalyzed arylation of N -tosyl- and N -nosylaldimines in methanol

AU - Chen, Chun Chih

AU - Gopula, Balraj

AU - Syu, Jin Fong

AU - Pan, Jhih Han

AU - Kuo, Ting Shen

AU - Wu, Ping Yu

AU - Henschke, Julian P.

AU - Wu, Hsyueh Liang

PY - 2014/9/5

Y1 - 2014/9/5

N2 - 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.

AB - 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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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

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Enantioselective and rapid Rh-catalyzed arylation of N -tosyl- and N -nosylaldimines in methanol

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