Simple Branched Sulfur–Olefins as Chiral Ligands for Rh-Catalyzed Asymmetric Arylation of Cyclic Ketimines: Highly Enantioselective Construction of Tetrasubstituted Carbon Stereocenters

New, simple, sulfinamide-based branched olefin ligands have been developed and successfully used in Rh-catalyzed asymmetric arylations of cyclic ketimines, providing efficient and highly enantioselective access to valuable benzosultams and benzosulfamidates containing a stereogenic quaternary carbon...

Full description

Saved in:
Bibliographic Details
Published in:Journal of the American Chemical Society 2013-01, Vol.135 (3), p.971-974
Main Authors: Wang, Hui, Jiang, Tao, Xu, Ming-Hua
Format: Article
Language:English
Subjects:
Alkenes - chemical synthesis
Alkenes - chemistry
Amides - chemistry
Carbon - chemistry
Catalysis
Imines - chemistry
Ligands
Models, Molecular
Molecular Structure
Nitriles - chemistry
Organometallic Compounds - chemistry
Rhodium - chemistry
Stereoisomerism
Sulfur - chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-a416t-4d630b7bb569f3ca453bd11507f566a84e54752df9ecb3ed0a43bdb7d0bfa4003
cites cdi_FETCH-LOGICAL-a416t-4d630b7bb569f3ca453bd11507f566a84e54752df9ecb3ed0a43bdb7d0bfa4003
container_end_page 974
container_issue 3
container_start_page 971
container_title Journal of the American Chemical Society
container_volume 135
creator Wang, Hui
Jiang, Tao
Xu, Ming-Hua
description New, simple, sulfinamide-based branched olefin ligands have been developed and successfully used in Rh-catalyzed asymmetric arylations of cyclic ketimines, providing efficient and highly enantioselective access to valuable benzosultams and benzosulfamidates containing a stereogenic quaternary carbon center. This is the first example of applying a sulfur–olefin ligand in catalytic asymmetric addition of imines.
doi_str_mv 10.1021/ja3110818
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1273806657</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1273806657</sourcerecordid><originalsourceid>FETCH-LOGICAL-a416t-4d630b7bb569f3ca453bd11507f566a84e54752df9ecb3ed0a43bdb7d0bfa4003</originalsourceid><addsrcrecordid>eNptkU1uFDEQhS0EIkNgwQWQN0iwaLD7f9gNrUAQI0ViwrpVdpczHrndg8uN1Ky4A8fhNpwEo0myYlWqqu-9Uukx9lyKN1Lk8u0BCilFK9sHbCWrXGSVzOuHbCWEyLOmrYsz9oTokNoyb-VjdpYX-bqVZbtiv3d2PDrk7wN4vceB72Zn5vDn568rh8Z64kC829sAjm_tDfiBuJkC_7LPOojglh9Js6FlHDEGq_kmLA6inTyfDO8W7dLsM0Y7Wo_0jl_am71b-IUHnyBChzra78i7yVMMs75TXic3oFlRtHGO6UQHQaXVLmLASaNPlZ6yRwYc4bPbes6-fri47i6z7dXHT91mm0Ep65iVQ10I1ShV1WtTaCirQg1SVqIxVV1DW2JVNlU-mDVqVeAgoEyAagahDJRCFOfs1cn3GKZvM1LsR0sanQOP00y9zJuiFXVdNQl9fUJ1mIgCmv4Y7Ahh6aXo_2XV32eV2Be3trMacbgn78JJwMsTAJr6wzQHn778j9Ff6WOgGw</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1273806657</pqid></control><display><type>article</type><title>Simple Branched Sulfur–Olefins as Chiral Ligands for Rh-Catalyzed Asymmetric Arylation of Cyclic Ketimines: Highly Enantioselective Construction of Tetrasubstituted Carbon Stereocenters</title><source>Access via American Chemical Society</source><creator>Wang, Hui ; Jiang, Tao ; Xu, Ming-Hua</creator><creatorcontrib>Wang, Hui ; Jiang, Tao ; Xu, Ming-Hua</creatorcontrib><description>New, simple, sulfinamide-based branched olefin ligands have been developed and successfully used in Rh-catalyzed asymmetric arylations of cyclic ketimines, providing efficient and highly enantioselective access to valuable benzosultams and benzosulfamidates containing a stereogenic quaternary carbon center. This is the first example of applying a sulfur–olefin ligand in catalytic asymmetric addition of imines.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja3110818</identifier><identifier>PMID: 23298148</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Alkenes - chemical synthesis ; Alkenes - chemistry ; Amides - chemistry ; Carbon - chemistry ; Catalysis ; Imines - chemistry ; Ligands ; Models, Molecular ; Molecular Structure ; Nitriles - chemistry ; Organometallic Compounds - chemistry ; Rhodium - chemistry ; Stereoisomerism ; Sulfur - chemistry</subject><ispartof>Journal of the American Chemical Society, 2013-01, Vol.135 (3), p.971-974</ispartof><rights>Copyright © 2013 American Chemical Society</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a416t-4d630b7bb569f3ca453bd11507f566a84e54752df9ecb3ed0a43bdb7d0bfa4003</citedby><cites>FETCH-LOGICAL-a416t-4d630b7bb569f3ca453bd11507f566a84e54752df9ecb3ed0a43bdb7d0bfa4003</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23298148$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wang, Hui</creatorcontrib><creatorcontrib>Jiang, Tao</creatorcontrib><creatorcontrib>Xu, Ming-Hua</creatorcontrib><title>Simple Branched Sulfur–Olefins as Chiral Ligands for Rh-Catalyzed Asymmetric Arylation of Cyclic Ketimines: Highly Enantioselective Construction of Tetrasubstituted Carbon Stereocenters</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>New, simple, sulfinamide-based branched olefin ligands have been developed and successfully used in Rh-catalyzed asymmetric arylations of cyclic ketimines, providing efficient and highly enantioselective access to valuable benzosultams and benzosulfamidates containing a stereogenic quaternary carbon center. This is the first example of applying a sulfur–olefin ligand in catalytic asymmetric addition of imines.</description><subject>Alkenes - chemical synthesis</subject><subject>Alkenes - chemistry</subject><subject>Amides - chemistry</subject><subject>Carbon - chemistry</subject><subject>Catalysis</subject><subject>Imines - chemistry</subject><subject>Ligands</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>Nitriles - chemistry</subject><subject>Organometallic Compounds - chemistry</subject><subject>Rhodium - chemistry</subject><subject>Stereoisomerism</subject><subject>Sulfur - chemistry</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNptkU1uFDEQhS0EIkNgwQWQN0iwaLD7f9gNrUAQI0ViwrpVdpczHrndg8uN1Ky4A8fhNpwEo0myYlWqqu-9Uukx9lyKN1Lk8u0BCilFK9sHbCWrXGSVzOuHbCWEyLOmrYsz9oTokNoyb-VjdpYX-bqVZbtiv3d2PDrk7wN4vceB72Zn5vDn568rh8Z64kC829sAjm_tDfiBuJkC_7LPOojglh9Js6FlHDEGq_kmLA6inTyfDO8W7dLsM0Y7Wo_0jl_am71b-IUHnyBChzra78i7yVMMs75TXic3oFlRtHGO6UQHQaXVLmLASaNPlZ6yRwYc4bPbes6-fri47i6z7dXHT91mm0Ep65iVQ10I1ShV1WtTaCirQg1SVqIxVV1DW2JVNlU-mDVqVeAgoEyAagahDJRCFOfs1cn3GKZvM1LsR0sanQOP00y9zJuiFXVdNQl9fUJ1mIgCmv4Y7Ahh6aXo_2XV32eV2Be3trMacbgn78JJwMsTAJr6wzQHn778j9Ff6WOgGw</recordid><startdate>20130123</startdate><enddate>20130123</enddate><creator>Wang, Hui</creator><creator>Jiang, Tao</creator><creator>Xu, Ming-Hua</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>20130123</creationdate><title>Simple Branched Sulfur–Olefins as Chiral Ligands for Rh-Catalyzed Asymmetric Arylation of Cyclic Ketimines: Highly Enantioselective Construction of Tetrasubstituted Carbon Stereocenters</title><author>Wang, Hui ; Jiang, Tao ; Xu, Ming-Hua</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a416t-4d630b7bb569f3ca453bd11507f566a84e54752df9ecb3ed0a43bdb7d0bfa4003</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Alkenes - chemical synthesis</topic><topic>Alkenes - chemistry</topic><topic>Amides - chemistry</topic><topic>Carbon - chemistry</topic><topic>Catalysis</topic><topic>Imines - chemistry</topic><topic>Ligands</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>Nitriles - chemistry</topic><topic>Organometallic Compounds - chemistry</topic><topic>Rhodium - chemistry</topic><topic>Stereoisomerism</topic><topic>Sulfur - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Hui</creatorcontrib><creatorcontrib>Jiang, Tao</creatorcontrib><creatorcontrib>Xu, Ming-Hua</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 the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Hui</au><au>Jiang, Tao</au><au>Xu, Ming-Hua</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Simple Branched Sulfur–Olefins as Chiral Ligands for Rh-Catalyzed Asymmetric Arylation of Cyclic Ketimines: Highly Enantioselective Construction of Tetrasubstituted Carbon Stereocenters</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2013-01-23</date><risdate>2013</risdate><volume>135</volume><issue>3</issue><spage>971</spage><epage>974</epage><pages>971-974</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><abstract>New, simple, sulfinamide-based branched olefin ligands have been developed and successfully used in Rh-catalyzed asymmetric arylations of cyclic ketimines, providing efficient and highly enantioselective access to valuable benzosultams and benzosulfamidates containing a stereogenic quaternary carbon center. This is the first example of applying a sulfur–olefin ligand in catalytic asymmetric addition of imines.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>23298148</pmid><doi>10.1021/ja3110818</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 0002-7863
ispartof Journal of the American Chemical Society, 2013-01, Vol.135 (3), p.971-974
issn 0002-7863
1520-5126
language eng
recordid cdi_proquest_miscellaneous_1273806657
source Access via American Chemical Society
subjects Alkenes - chemical synthesis
Alkenes - chemistry
Amides - chemistry
Carbon - chemistry
Catalysis
Imines - chemistry
Ligands
Models, Molecular
Molecular Structure
Nitriles - chemistry
Organometallic Compounds - chemistry
Rhodium - chemistry
Stereoisomerism
Sulfur - chemistry
title Simple Branched Sulfur–Olefins as Chiral Ligands for Rh-Catalyzed Asymmetric Arylation of Cyclic Ketimines: Highly Enantioselective Construction of Tetrasubstituted Carbon Stereocenters
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-03T19%3A26%3A03IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Simple%20Branched%20Sulfur%E2%80%93Olefins%20as%20Chiral%20Ligands%20for%20Rh-Catalyzed%20Asymmetric%20Arylation%20of%20Cyclic%20Ketimines:%20Highly%20Enantioselective%20Construction%20of%20Tetrasubstituted%20Carbon%20Stereocenters&rft.jtitle=Journal%20of%20the%20American%20Chemical%20Society&rft.au=Wang,%20Hui&rft.date=2013-01-23&rft.volume=135&rft.issue=3&rft.spage=971&rft.epage=974&rft.pages=971-974&rft.issn=0002-7863&rft.eissn=1520-5126&rft_id=info:doi/10.1021/ja3110818&rft_dat=%3Cproquest_cross%3E1273806657%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a416t-4d630b7bb569f3ca453bd11507f566a84e54752df9ecb3ed0a43bdb7d0bfa4003%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1273806657&rft_id=info:pmid/23298148&rfr_iscdi=true