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^*

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

46 引文斯高帕斯（Scopus）

摘要

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.

原文	英語
頁（從 - 到）	8077-8085
頁數	9
期刊	Journal of Organic Chemistry
卷	79
發行號	17
DOIs	https://doi.org/10.1021/jo5012653
出版狀態	已發佈 - 2014 9月 5

ASJC Scopus subject areas

有機化學

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10.1021/jo5012653

其它文件與鏈接

CCDC 1053835: Experimental Crystal Structure Determination
Chen, C.-C. (Creator), Gopula, B. (Creator), Syu, J.-F. (Creator), Pan, J.-H. (Creator), Kuo, T.-S. (Creator), Wu, P.-Y. (Creator), Henschke, J. P. (Creator) & Wu, H.-L. (Creator), Unknown Publisher, 2015
DOI: 10.5517/cc14clps, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc14clps&sid=DataCite
資料集: Dataset

引用此

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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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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

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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

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IS - 17

ER -

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

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 1053835: Experimental Crystal Structure Determination

引用此