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Enantioselective Synthesis of Tryptophan Derivatives by a Tandem Friedel–Crafts Conjugate Addition/Asymmetric Protonation Reaction

Kieffer, Madeleine E. and Repka, Lindsay M. and Reisman, Sarah E. (2012) Enantioselective Synthesis of Tryptophan Derivatives by a Tandem Friedel–Crafts Conjugate Addition/Asymmetric Protonation Reaction. Journal of the American Chemical Society, 134 (11). pp. 5131-5137. ISSN 0002-7863. PMCID PMC3310256. doi:10.1021/ja209390d. https://resolver.caltech.edu/CaltechAUTHORS:20120518-141739718

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Abstract

The tandem Friedel–Crafts conjugate addition/asymmetric protonation reaction between 2-substituted indoles and methyl 2-acetamidoacrylate is reported. The reaction is catalyzed by (R)-3,3′-dibromo-BINOL in the presence of stoichiometric SnCl_4, and is the first example of a tandem conjugate addition/asymmetric protonation reaction using a BINOL·SnCl_4 complex as the catalyst. A range of indoles furnished synthetic tryptophan derivatives in good yields and high levels of enantioselectivity, even on a preparative scale. The convergent nature of this transformation should lend itself to the preparation of unnatural tryptophan derivatives for use in a broad array of synthetic and biological applications.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja209390dDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja209390dPublisherArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3310256/PubMed CentralArticle
ORCID:
AuthorORCID
Reisman, Sarah E.0000-0001-8244-9300
Additional Information:© 2012 American Chemical Society. Published In Issue March 21, 2012; Article ASAP March 05, 2012; Received: October 05, 2011. We thank Prof. Brian Stoltz, Dr. Scott Virgil, and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment, and Dr. David VanderVelde for assistance with NMR structure determination. Fellowship support was provided by the NSF (M. E. K., Graduate Research Fellowship under Grant No. DGE-1144469) and the ACS Division of Organic Chemistry (L.M.R., sponsored by Genentech). Nadine Currie is acknowledged for assistance in the preparation of several indole substrates. Financial support from the California Institute of Technology, the NIH (NIGMS RGM097582A), and the donors of the ACS Petroleum Research Foundation are gratefully acknowledged.
Funders:
Funding AgencyGrant Number
NSF Graduate Research FellowshipDGE-1144469
American Chemical Society Division of Organic ChemistryUNSPECIFIED
CaltechUNSPECIFIED
NIHRGM097582A
American Chemical Society Petroleum Research FundUNSPECIFIED
Issue or Number:11
PubMed Central ID:PMC3310256
DOI:10.1021/ja209390d
Record Number:CaltechAUTHORS:20120518-141739718
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20120518-141739718
Official Citation:Enantioselective Synthesis of Tryptophan Derivatives by a Tandem Friedel–Crafts Conjugate Addition/Asymmetric Protonation Reaction Madeleine E. Kieffer, Lindsay M. Repka, and Sarah E. Reisman Journal of the American Chemical Society 2012 134 (11), 5131-5137
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:31544
Collection:CaltechAUTHORS
Deposited By: Jason Perez
Deposited On:18 May 2012 21:49
Last Modified:09 Nov 2021 19:55

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