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Published June 24, 2013 | Accepted Version + Supplemental Material
Journal Article Open

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


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).

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.

Attached Files

Accepted Version - nihms523185.pdf

Supplemental Material - anie_201301815_sm_miscellaneous_information.pdf


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