CaltechAUTHORS
  A Caltech Library Service

Enantioselective Synthesis of Pyrroloindolines by a Formal [3 + 2] Cycloaddition Reaction

Repka, Lindsay M. and Ni, Jane and Reisman, Sarah E. (2010) Enantioselective Synthesis of Pyrroloindolines by a Formal [3 + 2] Cycloaddition Reaction. Journal of the American Chemical Society, 132 (41). pp. 14418-14420. ISSN 0002-7863. PMCID PMC3222144. http://resolver.caltech.edu/CaltechAUTHORS:20101108-140057935

[img] PDF - Accepted Version
See Usage Policy.

1053Kb
[img] Crystallographic Info File (CIF) - Supplemental Material
See Usage Policy.

17Kb
[img] Crystallographic Info File (CIF) - Supplemental Material
See Usage Policy.

14Kb
[img]
Preview
PDF (Supporting Information 1 (Experimental Procedures)) - Supplemental Material
See Usage Policy.

3377Kb
[img] PDF (Supporting Information 2 (NMR Spectra)) - Supplemental Material
See Usage Policy.

1732Kb

Use this Persistent URL to link to this item: http://resolver.caltech.edu/CaltechAUTHORS:20101108-140057935

Abstract

(R)-BINOL•SnCl_4 was found to catalyze a formal [3 + 2] cycloaddition reaction between C(3)-substituted indoles and 2-amidoacrylates to provide pyrroloindolines. A variety of pyrroloindolines were prepared with high enantioselectivity in one step from simple precursors. This methodology is expected to facilitate the total synthesis of pyrroloindoline alkaloids, an important class of biologically active natural products.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja107328g DOIArticle
http://pubs.acs.org/doi/full/10.1021/ja107328gPublisherArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3222144/PubMed CentralArticle
ORCID:
AuthorORCID
Reisman, Sarah E.0000-0001-8244-9300
Additional Information:© 2010 American Chemical Society. Received August 23, 2010. Publication Date (Web): September 27, 2010. Published In Issue October 20, 2010 We thank Dr. Scott Virgil for insightful discussions; Drs. Michael Day and Larry Henling for X-ray crystallographic structural determination; and Prof. Brian Stoltz and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment. HRMS and X-ray crystallographic data were obtained on instruments purchased through awards to the California Institute of Technology by the NSF CRIF program (CHE- 0639094, CHE-0541745). NMR spectra were obtained on a spectrometer funded by the NIH (RR027690). Financial support from the California Institute of Technology and the Baxter Foundation is gratefully acknowledged. Supporting Information: Experimental details, characterization data, and NMR spectral charts. This material is available free of charge via the Internet at http://pubs.acs.org.
Funders:
Funding AgencyGrant Number
NSFCHE-0639094
NSFCHE-0541745
NIHRR027690
CaltechUNSPECIFIED
Baxter FoundationUNSPECIFIED
PubMed Central ID:PMC3222144
Record Number:CaltechAUTHORS:20101108-140057935
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20101108-140057935
Official Citation:Enantioselective Synthesis of Pyrroloindolines by a Formal [3 + 2] Cycloaddition Reaction Lindsay M. Repka, Jane Ni, Sarah E. Reisman Journal of the American Chemical Society 2010 132 (41), 14418-14420
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:20719
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:16 Nov 2010 20:10
Last Modified:31 Mar 2017 20:28

Repository Staff Only: item control page