Enantioselective Construction of α-Quaternary Cyclobutanones by Catalytic Asymmetric Allylic Alkylation

Reeves, Corey M. and Eidamshaus, Christian and Kim, Jimin and Stoltz, Brian M. (2013) Enantioselective Construction of α-Quaternary Cyclobutanones by Catalytic Asymmetric Allylic Alkylation. Angewandte Chemie International Edition, 52 (26). pp. 6718-6721. ISSN 1433-7851. PMCID PMC3817853. https://resolver.caltech.edu/CaltechAUTHORS:20130809-133957166

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Abstract

No strain, no gain! The first transition metal-catalyzed enantioselective α-alkylation of cyclobutanones is reported. This method employs palladium catalysis and an electron-deficient PHOX-type ligand to afford all-carbon α-quaternary cyclobutanones in good to excellent yields and enantioselectivities (see scheme).

Item Type:

Article

Related URLs:

URL	URL Type	Description
http://dx.doi.org/10.1002/anie.201301815	DOI	Article
http://dx.doi.org/10.1002/anie.201305706	DOI	Errata
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3817853/	PubMed Central	Article

ORCID:

Author	ORCID
Stoltz, Brian M.	0000-0001-9837-1528

Additional Information:

© 2013 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. Received: March 4, 2013; Revised: April 17, 2013; Published online: May 17, 2013. The authors wish to thank NIH-NIGMS (R01GM080269-01), Deutsche Forschungsgemeinschaft (DFG postdoctoral fellowship to C.E.), Amgen, Abbott, Boehringer Ingelheim, and Caltech for financial support. Materia, Inc. is gratefully acknowledged for the donation of catalysts. Dr. Mona Shahgholi and Naseem Torian are acknowledged for high-resolution mass spectrometry assistance. Jonny Gordon is acknowledged for insightful discussions. Robert Craig is gratefully acknowledged for providing compound L3 and for insightful discussion.

Funders:

Funding Agency	Grant Number
NIH	R01GM080269-01
Deutsche Forschungsgemeinschaft (DFG)	UNSPECIFIED
Amgen	UNSPECIFIED
Abbott	UNSPECIFIED
Boehringer Ingelheim	UNSPECIFIED
Caltech	UNSPECIFIED

Subject Keywords:

allylic alkylation; asymmetric catalysis; cyclobutanone; palladium; quaternary center

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PubMed Central ID:

PMC3817853

Record Number:

CaltechAUTHORS:20130809-133957166

Persistent URL:

https://resolver.caltech.edu/CaltechAUTHORS:20130809-133957166

Official Citation:

Reeves, C. M., Eidamshaus, C., Kim, J. and Stoltz, B. M. (2013), Enantioselective Construction of α-Quaternary Cyclobutanones by Catalytic Asymmetric Allylic Alkylation . Angew. Chem. Int. Ed., 52: 6718–6721. doi: 10.1002/anie.201301815

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ID Code:

39845

Collection:

CaltechAUTHORS

Deposited By:

Tony Diaz

Deposited On:

09 Aug 2013 20:57

Last Modified:

21 Apr 2020 23:58

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