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Published March 6, 2015 | Accepted Version + Supplemental Material
Journal Article Open

Enantioselective Synthesis of Dialkylated N-Heterocycles by Palladium-Catalyzed Allylic Alkylation


The enantioselective synthesis of α-disubstituted N-heterocyclic carbonyl compounds has been accomplished using palladium-catalyzed allylic alkylation. These catalytic conditions enable access to various heterocycles, such as morpholinone, thiomorpholinone, oxazolidin-4-one, 1,2-oxazepan-3-one, 1,3-oxazinan-4-one, and structurally related lactams, all bearing fully substituted α-positions. Broad functional group tolerance was explored at the α-position in the morpholinone series. We demonstrate the utility of this method by performing various transformations on our useful products to readily access a number of enantioenriched compounds.

Additional Information

© 2015 American Chemical Society. Received: November 25, 2014; revised: February 11, 2015. Publication Date (Web): February 25, 2015. The authors wish to thank NIH-NIGMS (R01GM080269 to B.M.S. and R01GM075962 to K.N.H), Amgen, the Gordon and Betty Moore Foundation, the Caltech Center for Catalysis and Chemical Synthesis, and Caltech for financial support. Y.N. thanks Toray Industries, Inc. for a postdoctoral fellowship. G.J.-O. and K.N.H. used the Extreme Science and Engineering Discovery Environment (XSEDE) supported by a grant (OCI-1053575) along with the UCLA Institute of Digital Research and Education (IDRE). The authors are grateful to Dr. Rina Dukor (BioTools) for helpful discussions. The authors thank Scott Virgil (Caltech) for instrumentation assistance and Dr. Douglas C. Behenna (Caltech) and Mr. Beau Pritchett (Caltech) for initial experimental results.

Attached Files

Accepted Version - nihms-1015128.pdf

Supplemental Material - ol503425t_si_001.pdf


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