Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to Five-, Six-, and Seven-Membered β-Substituted Cyclic Enones: Enantioselective Construction of All-Carbon Quaternary Stereocenters

Type
Article

Authors
Kikushima, Kotaro
Holder, Jeffrey C.
Gatti, Michele
Stoltz, Brian M.

KAUST Grant Number
KUS-11-006-02

Date
2011-05-11

Abstract
The first enantioselective Pd-catalyzed construction of all-carbon quaternary stereocenters via 1,4-addition of arylboronic acids to β-substituted cyclic enones is reported. Reaction of a wide range of arylboronic acids and cyclic enones using a catalyst prepared from Pd(OCOCF(3))(2) and a chiral pyridinooxazoline ligand yields enantioenriched products bearing benzylic stereocenters. Notably, this transformation is tolerant to air and moisture, providing a practical and operationally simple method of synthesizing enantioenriched all-carbon quaternary stereocenters.

Citation
Kikushima K, Holder JC, Gatti M, Stoltz BM (2011) Palladium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to Five-, Six-, and Seven-Membered β-Substituted Cyclic Enones: Enantioselective Construction of All-Carbon Quaternary Stereocenters. Journal of the American Chemical Society 133: 6902–6905. Available: http://dx.doi.org/10.1021/ja200664x.

Acknowledgements
This publication is based on work supported by Award No. KUS-11-006-02, made by King Abdullah University of Science and Technology (KAUST). The authors wish to thank NIH-NIGMS (R01GM080269-01), Amgen, Abbott, Boehringer Ingelheim, and Caltech for financial support. K.K. acknowledges the Japan Society for the Promotion of Science for a postdoctoral fellowship. M.G. is grateful to the Swiss National Science Foundation for financial support through a postdoctoral fellowship.

Publisher
American Chemical Society (ACS)

Journal
Journal of the American Chemical Society

DOI
10.1021/ja200664x

PubMed ID
21495647

PubMed Central ID
PMC3087848

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