Enantioselective and Rapid Rh-Catalyzed Arylation of N‑Tosyl- and N‑Nosylaldimines in Methanol

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 diarylme...

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Veröffentlicht in:	Journal of organic chemistry 2014-09, Vol.79 (17), p.8077-8085
Hauptverfasser:	Chen, Chun-Chih, Gopula, Balraj, Syu, Jin-Fong, Pan, Jhih-Han, Kuo, Ting-Shen, Wu, Ping-Yu, Henschke, Julian P, Wu, Hsyueh-Liang
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Sprache:	eng
Schlagworte:	Catalysis Methanol - chemistry Molecular Structure N-Methylaspartate - antagonists & inhibitors N-Methylaspartate - chemistry Rhodium - chemistry Stereoisomerism Tetrahydroisoquinolines - chemistry Tosyl Compounds - chemistry
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container_title	Journal of organic chemistry
container_volume	79
creator	Chen, Chun-Chih Gopula, Balraj Syu, Jin-Fong Pan, Jhih-Han Kuo, Ting-Shen Wu, Ping-Yu Henschke, Julian P Wu, Hsyueh-Liang
description	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.
doi_str_mv	10.1021/jo5012653
format	Article
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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. 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Org. Chem</addtitle><description>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.</description><subject>Catalysis</subject><subject>Methanol - chemistry</subject><subject>Molecular Structure</subject><subject>N-Methylaspartate - antagonists & inhibitors</subject><subject>N-Methylaspartate - chemistry</subject><subject>Rhodium - chemistry</subject><subject>Stereoisomerism</subject><subject>Tetrahydroisoquinolines - chemistry</subject><subject>Tosyl Compounds - chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkM1Kw0AUhQdRbK0ufAHJRtBFdH4yk3RZSv2BWkHqOtxMZuiUyaRmEiGufAVf0ScxsbUr7-IeDnz3wD0InRN8QzAlt-uSY0IFZwdoSDjFoRjj6BANMaY0ZFSwATrxfo274ZwfowHlJEoITYYomzlwtSm9skrW5l0F4PLgBTam26twCjXY9kPlwaRqLXSgC0odLL4_v5alb234i_d20VuwuSmMUz4wLnhS9QpcaU_RkQbr1dlOR-j1bracPoTz5_vH6WQeAktIHQIHTGKeaCAZjTqhSRYLTbnUeiykzCKqqSCZYDgaR5gxksSYj4mWwDTWgo3Q1TZ3U5VvjfJ1WhgvlbXgVNn4lHCBeZyQpEevt6isSu8rpdNNZQqo2pTgtK803VfasRe72CYrVL4n_zrsgMstANJ3d03lui__CfoBkop9xw</recordid><startdate>20140905</startdate><enddate>20140905</enddate><creator>Chen, Chun-Chih</creator><creator>Gopula, Balraj</creator><creator>Syu, Jin-Fong</creator><creator>Pan, Jhih-Han</creator><creator>Kuo, Ting-Shen</creator><creator>Wu, Ping-Yu</creator><creator>Henschke, Julian P</creator><creator>Wu, Hsyueh-Liang</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20140905</creationdate><title>Enantioselective and Rapid Rh-Catalyzed Arylation of N‑Tosyl- and N‑Nosylaldimines in Methanol</title><author>Chen, Chun-Chih ; Gopula, Balraj ; Syu, Jin-Fong ; Pan, Jhih-Han ; Kuo, Ting-Shen ; Wu, Ping-Yu ; Henschke, Julian P ; Wu, Hsyueh-Liang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-a5a01758fa1b248fa28b76f25cff96ccb42f261b6304940331870591fca3f0f63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Catalysis</topic><topic>Methanol - chemistry</topic><topic>Molecular Structure</topic><topic>N-Methylaspartate - antagonists & inhibitors</topic><topic>N-Methylaspartate - chemistry</topic><topic>Rhodium - chemistry</topic><topic>Stereoisomerism</topic><topic>Tetrahydroisoquinolines - chemistry</topic><topic>Tosyl Compounds - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chen, Chun-Chih</creatorcontrib><creatorcontrib>Gopula, Balraj</creatorcontrib><creatorcontrib>Syu, Jin-Fong</creatorcontrib><creatorcontrib>Pan, Jhih-Han</creatorcontrib><creatorcontrib>Kuo, Ting-Shen</creatorcontrib><creatorcontrib>Wu, Ping-Yu</creatorcontrib><creatorcontrib>Henschke, Julian P</creatorcontrib><creatorcontrib>Wu, Hsyueh-Liang</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chen, Chun-Chih</au><au>Gopula, Balraj</au><au>Syu, Jin-Fong</au><au>Pan, Jhih-Han</au><au>Kuo, Ting-Shen</au><au>Wu, Ping-Yu</au><au>Henschke, Julian P</au><au>Wu, Hsyueh-Liang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective and Rapid Rh-Catalyzed Arylation of N‑Tosyl- and N‑Nosylaldimines in Methanol</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2014-09-05</date><risdate>2014</risdate><volume>79</volume><issue>17</issue><spage>8077</spage><epage>8085</epage><pages>8077-8085</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><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.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>25148128</pmid><doi>10.1021/jo5012653</doi><tpages>9</tpages></addata></record>
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subjects	Catalysis Methanol - chemistry Molecular Structure N-Methylaspartate - antagonists & inhibitors N-Methylaspartate - chemistry Rhodium - chemistry Stereoisomerism Tetrahydroisoquinolines - chemistry Tosyl Compounds - chemistry
title	Enantioselective and Rapid Rh-Catalyzed Arylation of N‑Tosyl- and N‑Nosylaldimines in Methanol
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