Catalytic Asymmetric Acyl Halide−Aldehyde Cyclocondensation Reactions of Substituted Ketenes

Catalytic asymmetric acyl halide−aldehyde cyclocondensation (AAC) reactions of alkyl-substituted ketenes with structurally diverse aldehydes provide cis-disubstituted β-lactones with high enantioselectivity. The AAC reactions utilize a novel Al(III)-triamine catalyst in which the metal's dynami...

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Veröffentlicht in:	Journal of the American Chemical Society 2004-01, Vol.126 (1), p.14-15
Hauptverfasser:	Nelson, Scott G, Zhu, Cheng, Shen, Xiaoqiang
Format:	Artikel
Sprache:	eng
Schlagworte:	Aldehydes - chemistry Catalysis Chemistry Cyclization Exact sciences and technology Hydrocarbons, Brominated - chemistry Ketones - chemistry Lactones - chemical synthesis Models, Molecular Organic chemistry
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container_title	Journal of the American Chemical Society
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creator	Nelson, Scott G Zhu, Cheng Shen, Xiaoqiang
description	Catalytic asymmetric acyl halide−aldehyde cyclocondensation (AAC) reactions of alkyl-substituted ketenes with structurally diverse aldehydes provide cis-disubstituted β-lactones with high enantioselectivity. The AAC reactions utilize a novel Al(III)-triamine catalyst in which the metal's dynamic coordination geometry leads to a highly selective catalyst complex. These AAC reactions represent a functional solution to highly enantioselective substituted ester enolate aldol additions.
doi_str_mv	10.1021/ja0391208
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These AAC reactions represent a functional solution to highly enantioselective substituted ester enolate aldol additions.</description><subject>Aldehydes - chemistry</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>Cyclization</subject><subject>Exact sciences and technology</subject><subject>Hydrocarbons, Brominated - chemistry</subject><subject>Ketones - chemistry</subject><subject>Lactones - chemical synthesis</subject><subject>Models, Molecular</subject><subject>Organic chemistry</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0Mtu1DAUBmALgei0sOAFUDYgdZHWt8TOcoigU7VSES1brGPnWGTIpdiORN6ANY_Ik5DRjDobVj7W-fTr6CfkDaMXjHJ2uQUqKsapfkZWrOA0Lxgvn5MVpZTnSpfihJzGuF2-kmv2kpwwqWhFRbki32pI0M2pddk6zn2PKexGN3fZBrq2wb-__6y7Br_PDWb17LrRjUODQ4TUjkP2BcHthpiNPrufbExtmhI22Q0mHDC-Ii88dBFfH94z8vXTx4d6k9_eXV3X69scpCxSXlkvCqUqznRZVEJygUxJbjVI63klvfVlwbyuOJTCNqUF1lh01lNFlQQrzsj7fe5jGH9OGJPp2-iw62DAcYpGU6o5p2KB53vowhhjQG8eQ9tDmA2jZlemeSpzsW8PoZPtsTnKQ3sLeHcAEB10PsDg2nh0hWRMcr64fO_amPDX0x7CD1MqoQrz8PneiM1NrfQHaa6OueCi2Y5TGJbu_nPgP6y0l9g</recordid><startdate>20040114</startdate><enddate>20040114</enddate><creator>Nelson, Scott G</creator><creator>Zhu, Cheng</creator><creator>Shen, Xiaoqiang</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><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>20040114</creationdate><title>Catalytic Asymmetric Acyl Halide−Aldehyde Cyclocondensation Reactions of Substituted Ketenes</title><author>Nelson, Scott G ; Zhu, Cheng ; Shen, Xiaoqiang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a445t-9bf357792186593423e1742b8a4bf294fbf651f892a63bd6ba1dbecbf07074ab3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Aldehydes - chemistry</topic><topic>Catalysis</topic><topic>Chemistry</topic><topic>Cyclization</topic><topic>Exact sciences and technology</topic><topic>Hydrocarbons, Brominated - chemistry</topic><topic>Ketones - chemistry</topic><topic>Lactones - chemical synthesis</topic><topic>Models, Molecular</topic><topic>Organic chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nelson, Scott G</creatorcontrib><creatorcontrib>Zhu, Cheng</creatorcontrib><creatorcontrib>Shen, Xiaoqiang</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><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>Nelson, Scott G</au><au>Zhu, Cheng</au><au>Shen, Xiaoqiang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Catalytic Asymmetric Acyl Halide−Aldehyde Cyclocondensation Reactions of Substituted Ketenes</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. 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subjects	Aldehydes - chemistry Catalysis Chemistry Cyclization Exact sciences and technology Hydrocarbons, Brominated - chemistry Ketones - chemistry Lactones - chemical synthesis Models, Molecular Organic chemistry
title	Catalytic Asymmetric Acyl Halide−Aldehyde Cyclocondensation Reactions of Substituted Ketenes
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