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

45 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

存取文件

10.1021/jo5012653

其它文件與鏈接

CCDC 1053835: Experimental Crystal Structure Determination
Chen, C. (Creator), Gopula, B. (Creator), Syu, J. (Creator), Pan, J. (Creator), Kuo, T. (Creator), Wu, P. (Creator), Henschke, J. P. (Creator) & Wu, H. (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

@article{ce9f6a0bc96246de830f8cdf838c31d1,

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}",

note = "Publisher Copyright: {\textcopyright} 2014 American Chemical Society.",

year = "2014",

month = sep,

day = "5",

doi = "10.1021/jo5012653",

language = "English",

volume = "79",

pages = "8077--8085",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "17",

}

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=84922604750&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84922604750&partnerID=8YFLogxK

U2 - 10.1021/jo5012653

DO - 10.1021/jo5012653

M3 - Article

C2 - 25148128

AN - SCOPUS:84922604750

SN - 0022-3263

VL - 79

SP - 8077

EP - 8085

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

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