Construction of Vicinal Tertiary and All-Carbon Quaternary Stereocenters via Ir-Catalyzed Regio-, Diastereo-, and Enantioselective Allylic Alkylation and Applications in Sequential Pd Catalysis

Liu, Wen-Bo and Reeves, Corey M. and Virgil, Scott C. and Stoltz, Brian M. (2013) Construction of Vicinal Tertiary and All-Carbon Quaternary Stereocenters via Ir-Catalyzed Regio-, Diastereo-, and Enantioselective Allylic Alkylation and Applications in Sequential Pd Catalysis. Journal of the American Chemical Society, 135 (29). pp. 10626-10629. ISSN 0002-7863. PMCID PMC3756902. doi:10.1021/ja4052075. https://resolver.caltech.edu/CaltechAUTHORS:20131002-102340513

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Abstract

Highly congested vicinal stereocenters comprised of tertiary and all-carbon quaternary centers were generated via Ir-catalyzed asymmetric allylic alkylation of β-ketoesters. These catalytic reactions proceed in excellent yields with a broad scope on either reaction partner and with outstanding regio-, diastereo-, and enantiocontrol. Implementation of a subsequent Pd-catalyzed alkylation affords dialkylated products with pinpoint stereochemical control of both chiral centers.

Item Type:

Article

Related URLs:

URL	URL Type	Description
http://dx.doi.org/10.1021/ja4052075	DOI	Article
http://pubs.acs.org/doi/abs/10.1021/ja4052075	Publisher	Article
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3756902/	PubMed Central	Article

ORCID:

Author	ORCID
Liu, Wen-Bo	0000-0003-2687-557X
Virgil, Scott C.	0000-0001-8586-5641
Stoltz, Brian M.	0000-0001-9837-1528

Additional Information:

© 2013 American Chemical Society. Received: May 23, 2013; Published: July 7, 2013. The authors wish to thank NIH-NIGMS (R01GM080269), Amgen, the Gordon and Betty Moore Foundation, and Caltech for financial support. Shanghai Institute of Organic Chemistry (SIOC) is thanked for a postdoctoral fellowship to W.-B.L. Dr. Mona Shahgholi and Naseem Torian are acknowledged for mass spectrometry assistance. Lawrence Henling is acknowledged for X-ray crystallographic structural determination. The authors thank Mr. Jeff Holder for the preparation of [Ir(cod)Cl]2. The authors are thankful to Professor Shu-Li You and Mr. Robert Craig for L3 and (R)-L8, respectively, and for helpful discussions.

Funders:

Funding Agency	Grant Number
NIH	R01GM080269
Amgen	UNSPECIFIED
Gordon and Betty Moore Foundation	UNSPECIFIED
Caltech	UNSPECIFIED
Shanghai Institute of Organic Chemistry (SIOC)	UNSPECIFIED

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PubMed Central ID:

PMC3756902

DOI:

10.1021/ja4052075

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CaltechAUTHORS:20131002-102340513

Persistent URL:

https://resolver.caltech.edu/CaltechAUTHORS:20131002-102340513

Official Citation:

Construction of Vicinal Tertiary and All-Carbon Quaternary Stereocenters via Ir-Catalyzed Regio-, Diastereo-, and Enantioselective Allylic Alkylation and Applications in Sequential Pd Catalysis Wen-Bo Liu, Corey M. Reeves, Scott C. Virgil, and Brian M. Stoltz Journal of the American Chemical Society 2013 135 (29), 10626-10629

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ID Code:

41606

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CaltechAUTHORS

Deposited By:

Tony Diaz

Deposited On:

02 Oct 2013 21:28

Last Modified:

10 Nov 2021 04:32

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