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Published July 8, 2014 | Accepted Version + Supplemental Material
Journal Article Open

Palladium-catalyzed decarboxylative allylic alkylation of diastereomeric β-ketoesters


The palladium-catalyzed decarboxylative allylic alkylation of diastereomeric β-ketoesters derived from 4-tert-butylcyclohexanone is described. These experiments were performed to elucidate our understanding of stereoablative enantioconvergent catalysis. A detailed analysis of the product distribution, including stereochemical outcome of the products, is included. These studies also reveal an interesting example of selectivity that is governed by competing modes of substrate and catalyst control.

Additional Information

© 2014 Elsevier Ltd. Received 21 February 2014; Received in revised form 10 March 2014; Accepted 12 March 2014; Available online 18 March 2014. Dedicated to Professor Sarah Reisman on receipt of the Tetrahedron Young Investigator Award. The authors wish to thank NIH-NIGMS (R01GM080269), Abbott Laboratories (_100001316), Amgen (_100002429),Merck, Bristol-Myers Squibb (_100002491), Boehringer Ingelheim (_100001003), the Gordon and Betty Moore Foundation (_100000936) and Caltech for financial support. C.M.R. gratefully acknowledges the Rose Hill Foundation for pre-doctoral funding. R.A.C. gratefully acknowledges the support of this work provided by a fellowship from the National Cancer Institute of the National Institutes of Health (_100000002) under Award Number F31CA174359. Mr. Lawrence Henling and Dr. Michael Day are gratefully acknowledged for Xray crystallographic structural determination. The Bruker KAPPA APEXII X-ray diffractometer was purchased via an NSF CRIF:MU award to the California Institute of Technology, CHE-0639094.

Attached Files

Accepted Version - nihms585845.pdf

Supplemental Material - mmc1.pdf


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