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Enantioselective Synthesis of Polycyclic Nitrogen Heterocycles by Rh-Catalyzed Alkene Hydroacylation: Constructing Six-Membered Rings in the Absence of Chelation Assistance
Organic Letters
  • Xiang-Wei Du, Iowa State University
  • Avipsa Ghosh, Iowa State University
  • Levi M. Stanley, Iowa State University
Document Type
Article
Disciplines
Publication Version
Published Version
Publication Date
7-1-2014
DOI
10.1021/ol501869s
Abstract
Catalytic, enantioselective hydroacylations of N-allylindole-2-carboxaldehydes and N-allylpyrrole-2-carboxaldehydes are reported. In contrast to many alkene hydroacylations that form six-membered rings, these annulative processes occur in the absence of ancillary functionality to stabilize the acylrhodium(III) hydride intermediate. The intramolecular hydroacylation reactions generate 7,8-dihydropyrido[1,2-a]indol-9(6H)ones and 6,7-dihydroindolizin-8(5H)-ones in moderate to high yields with excellent enantioselectivities.
Comments

This article is from Organic Letters 16 (2014): 4036, doi:10.1021/ol501869s. Posted with permission.

Rights
This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.
Copyright Owner
American Chemical Society
Language
en
File Format
application/pdf
Citation Information
Xiang-Wei Du, Avipsa Ghosh and Levi M. Stanley. "Enantioselective Synthesis of Polycyclic Nitrogen Heterocycles by Rh-Catalyzed Alkene Hydroacylation: Constructing Six-Membered Rings in the Absence of Chelation Assistance" Organic Letters Vol. 16 Iss. 15 (2014) p. 4036 - 4039
Available at: http://works.bepress.com/levi_stanley/5/