Enantioselective Addition of Boronates to o‑Quinone Methides Catalyzed by Chiral Biphenols

Chiral biphenols were found to catalyze the enantioselective asymmetric addition of aryl- or alkenylboronates to o-quinone methides. Substituted 2-styryl phenols were obtained in good yields (up to 95%) with high enantiomeric ratios (up to 98:2) in the presence of 10 mol % 3,3′-Br2-BINOL. A two-step...

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Veröffentlicht in:	Journal of the American Chemical Society 2012-12, Vol.134 (49), p.19965-19968
Hauptverfasser:	Luan, Yi, Schaus, Scott E
Format:	Artikel
Sprache:	eng
Schlagworte:	Benzoquinones - chemical synthesis Benzoquinones - chemistry Boronic Acids - chemistry Catalysis Indolequinones - chemistry Molecular Structure Phenols - chemical synthesis Phenols - chemistry Stereoisomerism
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container_title	Journal of the American Chemical Society
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creator	Luan, Yi Schaus, Scott E
description	Chiral biphenols were found to catalyze the enantioselective asymmetric addition of aryl- or alkenylboronates to o-quinone methides. Substituted 2-styryl phenols were obtained in good yields (up to 95%) with high enantiomeric ratios (up to 98:2) in the presence of 10 mol % 3,3′-Br2-BINOL. A two-step synthesis of (S)-4-methoxydalbergione in good yield and selectivity was achieved.
doi_str_mv	10.1021/ja309076g
format	Article
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Am. Chem. Soc</addtitle><description>Chiral biphenols were found to catalyze the enantioselective asymmetric addition of aryl- or alkenylboronates to o-quinone methides. Substituted 2-styryl phenols were obtained in good yields (up to 95%) with high enantiomeric ratios (up to 98:2) in the presence of 10 mol % 3,3′-Br2-BINOL. A two-step synthesis of (S)-4-methoxydalbergione in good yield and selectivity was achieved.</description><subject>Benzoquinones - chemical synthesis</subject><subject>Benzoquinones - chemistry</subject><subject>Boronic Acids - chemistry</subject><subject>Catalysis</subject><subject>Indolequinones - chemistry</subject><subject>Molecular Structure</subject><subject>Phenols - chemical synthesis</subject><subject>Phenols - chemistry</subject><subject>Stereoisomerism</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkE9LwzAYxoMobk4PfgHJRdBDNUnbNDm6Mv_ARAS9CSVN3rqMLplNK8yTX8Gv6CexsrmTp5fn4ccP3gehY0ouKGH0cq5iIknGX3fQkKaMRCllfBcNCSEsygSPB-gghHkfEyboPhqwmBFOZTZELxOnXGt9gBp0a98BXxlj-8JhX-Gxb7xTLQTceuy_P78eO-u8A3wP7cyavs9Vq-rVBxhcrnA-s42q8dguZ-B8HQ7RXqXqAEebO0LP15On_DaaPtzc5VfTSCWUt5HgRJMkIUJIISqtGaWEA81AGl5VmUxkVRqdGZ2WKU-YllylGpiSYHQiaBaP0Nnau2z8WwehLRY2aKhr5cB3oaAsFpSkMhY9er5GdeNDaKAqlo1dqGZVUFL8jllsx-zZk422KxdgtuTfej1wugaUDsXcd43rv_xH9ANusnw3</recordid><startdate>20121212</startdate><enddate>20121212</enddate><creator>Luan, Yi</creator><creator>Schaus, Scott E</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>20121212</creationdate><title>Enantioselective Addition of Boronates to o‑Quinone Methides Catalyzed by Chiral Biphenols</title><author>Luan, Yi ; Schaus, Scott E</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a416t-860c044088988fcc21106e17e9d6ff7949fbdc7dc5b5642c96a5ce2a9edc48173</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Benzoquinones - chemical synthesis</topic><topic>Benzoquinones - chemistry</topic><topic>Boronic Acids - chemistry</topic><topic>Catalysis</topic><topic>Indolequinones - chemistry</topic><topic>Molecular Structure</topic><topic>Phenols - chemical synthesis</topic><topic>Phenols - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Luan, Yi</creatorcontrib><creatorcontrib>Schaus, Scott E</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>Luan, Yi</au><au>Schaus, Scott E</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective Addition of Boronates to o‑Quinone Methides Catalyzed by Chiral Biphenols</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. 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subjects	Benzoquinones - chemical synthesis Benzoquinones - chemistry Boronic Acids - chemistry Catalysis Indolequinones - chemistry Molecular Structure Phenols - chemical synthesis Phenols - chemistry Stereoisomerism
title	Enantioselective Addition of Boronates to o‑Quinone Methides Catalyzed by Chiral Biphenols
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