Palladium-Catalyzed Asymmetric Quaternary Stereocenter Formation

An efficient palladium catalyst is presented for the formation of benzylic quaternary stereocenters by conjugate addition of arylboronic acids to a variety of β,β‐disubstituted carbocyclic, heterocyclic, and acyclic enones. The catalyst is readily prepared from PdCl2, PhBOX, and AgSbF6, and provides...

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Veröffentlicht in:	Chemistry : a European journal Jg. 18; H. 22; S. 6907 - 6914
Hauptverfasser:	Gottumukkala, Aditya L., Matcha, Kiran, Lutz, Martin, de Vries , Johannes G., Minnaard, Adriaan J.
Format:	Journal Article
Sprache:	Englisch
Veröffentlicht:	Weinheim WILEY-VCH Verlag 29.05.2012 WILEY‐VCH Verlag Wiley Wiley Subscription Services, Inc
Schlagworte:	arylboronic acids Asymmetry Boronic Acids - chemical synthesis Boronic Acids - chemistry Catalysis Catalysts Chemistry Chemistry, Multidisciplinary Conjugates cuparenone Formations Michael addition Molecular Structure Palladium Palladium - chemistry Physical Sciences quaternary stereocenters Science & Technology Sesquiterpenes - chemical synthesis Sesquiterpenes - chemistry Stereoisomerism Strategy Michael addition ENANTIOSELECTIVE SYNTHESIS ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS SUBSTITUTED CYCLIC ENONES TRISUBSTITUTED ENONES arylboronic acids quaternary stereocenters cuparenone CONSTRUCTION palladium STEREOGENIC CENTERS PALLADIUM(II)-CATALYZED 1,4-ADDITION ARYL ALUMINUM REAGENTS CONJUGATE ADDITION
ISSN:	0947-6539, 1521-3765, 1521-3765
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Zusammenfassung:	An efficient palladium catalyst is presented for the formation of benzylic quaternary stereocenters by conjugate addition of arylboronic acids to a variety of β,β‐disubstituted carbocyclic, heterocyclic, and acyclic enones. The catalyst is readily prepared from PdCl2, PhBOX, and AgSbF6, and provides products in up to 99 % enantiomeric excess, with good yields. Based on this strategy, (−)‐α‐cuparenone has been prepared in only two steps. Jack of all trades: An efficient Pd catalyst for the formation of benzylic quaternary stereocenters by conjugate addition of arylboronic acids to a variety of β,β‐disubstituted cyclic and acyclic enones is presented (see scheme). The catalyst provides product enantioselectivities up to 99 %.
Bibliographie:	Netherlands Ministry of Education, Culture and Science SmartMix Program of the Netherlands Ministry of Economic Affairs ark:/67375/WNG-D1W5LX95-D istex:94A9126A0FBDAAC9C2C1BCD15200E90A3701F736 CatchBio Program - No. 053.70.206 ArticleID:CHEM201200694 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 content type line 23
ISSN:	0947-6539 1521-3765 1521-3765
DOI:	10.1002/chem.201200694