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Enantio-, Diastereo-, and Regioselective Iridium-Catalyzed Asymmetric Allylic Alkylation of Acyclic β-Ketoesters

Liu, Wen-Bo and Reeves, Corey M. and Stoltz, Brian M. (2013) Enantio-, Diastereo-, and Regioselective Iridium-Catalyzed Asymmetric Allylic Alkylation of Acyclic β-Ketoesters. Journal of the American Chemical Society, 135 (46). pp. 17298-17301. ISSN 0002-7863. PMCID PMC3881553. https://resolver.caltech.edu/CaltechAUTHORS:20140106-104251997

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Abstract

The first regio-, diastereo-, and enantioselective allylic alkylation of acyclic β-ketoesters to form vicinal tertiary and all-carbon quaternary stereocenters is reported. Critical to the successful development of this method was the employment of iridium catalysis in concert with N-aryl-phosphoramidite ligands. Broad functional group tolerance is observed at the keto-, ester-, and α-positions of the nucleophile. Various transformations demonstrating the utility of this method for rapidly accessing complex enantioenriched compounds are reported.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja4097829 DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja4097829PublisherArticle
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3881553/PubMed CentralArticle
ORCID:
AuthorORCID
Liu, Wen-Bo0000-0003-2687-557X
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2013 American Chemical Society. Received: September 20, 2013; Published: October 28, 2013. The authors wish to thank NIH-NIGMS (R01GM080269), Amgen, the Gordon and Betty Moore Foundation, the Caltech Center for Catalysis and Chemical Synthesis, and Caltech for financial support. Shanghai Institute of Organic Chemistry (SIOC) is thanked for a postdoctoral fellowship to W.-B.L. Lawrence Henling is acknowledged for X-ray crystallographic structural determination. We thank the reviewers for the valuable suggestions about the Hammett correlation and Brown σ+ constants.
Funders:
Funding AgencyGrant Number
NIHR01GM080269
AmgenUNSPECIFIED
Gordon and Betty Moore FoundationUNSPECIFIED
Caltech Center for Catalysis and Chemical SynthesisUNSPECIFIED
Shanghai Institute of Organic Chemistry (SIOC)UNSPECIFIED
Issue or Number:46
PubMed Central ID:PMC3881553
Record Number:CaltechAUTHORS:20140106-104251997
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20140106-104251997
Official Citation:Enantio-, Diastereo-, and Regioselective Iridium-Catalyzed Asymmetric Allylic Alkylation of Acyclic β-Ketoesters Wen-Bo Liu, Corey M. Reeves, and Brian M. Stoltz Journal of the American Chemical Society 2013 135 (46), 17298-17301
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:43225
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:09 Jan 2014 16:14
Last Modified:03 Oct 2019 06:05

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