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.
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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. | ||||||||||||
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Issue or Number: | 29 | ||||||||||||
PubMed Central ID: | PMC3756902 | ||||||||||||
DOI: | 10.1021/ja4052075 | ||||||||||||
Record Number: | 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 | ||||||||||||
Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||||||||
ID Code: | 41606 | ||||||||||||
Collection: | CaltechAUTHORS | ||||||||||||
Deposited By: | Tony Diaz | ||||||||||||
Deposited On: | 02 Oct 2013 21:28 | ||||||||||||
Last Modified: | 10 Nov 2021 04:32 |
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