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Palladium-catalyzed asymmetric quaternary stereocenter formation.
Chemistry. 2012 May 29; 18(22):6907-14.C

Abstract

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 PdCl(2), PhBOX, and AgSbF(6), 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.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Gottumukkala AL
Stratingh Institute for Chemistry, University of Groningen, Groningen, The Netherlands.
Matcha K
No affiliation info available
Lutz M
No affiliation info available
de Vries JG
No affiliation info available
Minnaard AJ
No affiliation info available

MeSH

Boronic AcidsCatalysisMolecular StructurePalladiumSesquiterpenesStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

22532469

Citation

Gottumukkala, Aditya L., et al. "Palladium-catalyzed Asymmetric Quaternary Stereocenter Formation." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 18, no. 22, 2012, pp. 6907-14.
Gottumukkala AL, Matcha K, Lutz M, et al. Palladium-catalyzed asymmetric quaternary stereocenter formation. Chemistry. 2012;18(22):6907-14.
Gottumukkala, A. L., Matcha, K., Lutz, M., de Vries, J. G., & Minnaard, A. J. (2012). Palladium-catalyzed asymmetric quaternary stereocenter formation. Chemistry (Weinheim an Der Bergstrasse, Germany), 18(22), 6907-14. https://doi.org/10.1002/chem.201200694
Gottumukkala AL, et al. Palladium-catalyzed Asymmetric Quaternary Stereocenter Formation. Chemistry. 2012 May 29;18(22):6907-14. PubMed PMID: 22532469.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium-catalyzed asymmetric quaternary stereocenter formation. AU - Gottumukkala,Aditya L, AU - Matcha,Kiran, AU - Lutz,Martin, AU - de Vries,Johannes G, AU - Minnaard,Adriaan J, Y1 - 2012/04/24/ PY - 2012/03/01/received PY - 2012/4/26/entrez PY - 2012/4/26/pubmed PY - 2012/10/30/medline SP - 6907 EP - 14 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 18 IS - 22 N2 - 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 PdCl(2), PhBOX, and AgSbF(6), 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. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/22532469/Palladium_catalyzed_asymmetric_quaternary_stereocenter_formation_ L2 - https://doi.org/10.1002/chem.201200694 DB - PRIME DP - Unbound Medicine ER -