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Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Acyclic α-N-Pyrrolyl/Indolyl Ketones

Lavernhe, Rémi and Alexy, Eric J. and Zhang, Haiming and Stoltz, Brian M. (2020) Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Acyclic α-N-Pyrrolyl/Indolyl Ketones. Organic Letters, 22 (11). pp. 4272-4275. ISSN 1523-7060. https://resolver.caltech.edu/CaltechAUTHORS:20200519-093555551

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Abstract

The synthesis of fully substituted α-N-pyrrolyl and indolyl ketones via enantioselective palladium-catalyzed allylic alkylation is described. The acyclic ketones are alkylated in high yields with high enantioselectivities through the use of an electron-deficient phosphinooxazoline ligand, furnishing a highly congested and synthetically challenging stereocenter. The obtained alkylation products contain multiple reactive sites poised for additional functionalizations and diversification.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/acs.orglett.0c01303DOIArticle
ORCID:
AuthorORCID
Alexy, Eric J.0000-0002-2971-9698
Zhang, Haiming0000-0002-2139-2598
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2020 American Chemical Society. Received: April 14, 2020; Published: May 18, 2020. We thank the NIH-NIGMS (R01GM080269), the Gordon and Betty Moore Foundation, and Caltech for financial support. E.J.A. thanks the National Science Foundation for a predoctoral fellowship. We thank Dr. David VanderVelde (Caltech) for NMR expertise. Dr. Scott Virgil (Caltech Center for Catalysis and Chemical Synthesis) is thanked for instrumentation and SFC assistance. Dr. Michael Takase (Caltech) and Lawrence Henling (Caltech) are acknowledged for X-ray analysis. The authors declare no competing financial interest.
Funders:
Funding AgencyGrant Number
NIHR01GM080269
Gordon and Betty Moore FoundationUNSPECIFIED
CaltechUNSPECIFIED
NSF Predoctoral FellowshipUNSPECIFIED
Issue or Number:11
Record Number:CaltechAUTHORS:20200519-093555551
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20200519-093555551
Official Citation:Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Acyclic α-N-Pyrrolyl/Indolyl Ketones. Remi Lavernhe, Eric J. Alexy, Haiming Zhang, and Brian M. Stoltz. Organic Letters 2020 22 (11), 4272-4275 DOI: 10.1021/acs.orglett.0c01303
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:103305
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:19 May 2020 16:42
Last Modified:08 Jun 2020 21:43

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