Prev. Article Next Article Table of Contents

Letter

Amine-Promoted, Organocatalytic Aziridination of Enones

Supporting Info

Alan Armstrong,*^† Carl A. Baxter,^† Scott G. Lamont,^‡ Andrew R. Pape,^‡ and Richard Wincewicz^†

Department of Chemistry, Imperial College London, South Kensington, London, SW7 2AZ, United Kingdom, and AstraZeneca, Mereside, Alderley Park, Macclesfield, Cheshire, SK10 4TG, United Kingdom

Org. Lett., 2007, 9 (2), pp 351–353

DOI: 10.1021/ol062852v

Publication Date (Web): December 16, 2006

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

†

Imperial College London.

‡

AstraZeneca.

, a.armstrong@imperial.ac.uk

Abstract

A novel method is presented using N−N ylides (prepared by in situ amination of a tertiary amine) for the aziridination of a range of enone systems. The amine may be used sub-stoichiometrically, and promising levels of enantioselectivity are observed with quinine as promoter.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue January 18, 2007
Received November 23, 2006

Recommend & Share

Related Content

Synthesis and Reactivity of C-Heteroatom-Substituted AziridinesChemical Reviews
- Synthesis and Reactivity of C-Heteroatom-Substituted Aziridines
  Girija S. Singh, Matthias D'hooghe, and Norbert De Kimpe
  Chemical Reviews 2007 107 (5), pp 2080–2135
  Abstract | Full Text HTML | Hi-Res PDF
Asymmetric Synthesis of Diamine Derivatives via Sequential Palladium and Rhodium CatalysisJournal of the American Chemical Society
- Asymmetric Synthesis of Diamine Derivatives via Sequential Palladium and Rhodium Catalysis
  Barry M. Trost, Sushant Malhotra, David E. Olson, Autumn Maruniak and J. Du Bois
  Journal of the American Chemical Society 2009 131 (12), pp 4190–4191
  Abstract: The use of a bifunctional nitrogen nucleophile and an allyl carbonate starting material in successive enantioselective palladium- and diastereoselective rhodium-catalyzed reactions enables the rapid assembly of unique amino aziridine products. Further ...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF
Enantioselective Catalytic Aziridinations and Asymmetric Nitrene Insertions into CH BondsChemical Reviews
- Enantioselective Catalytic Aziridinations and Asymmetric Nitrene Insertions into CH Bonds
  Paul Müller and Corinne Fruit
  Chemical Reviews 2003 103 (8), pp 2905–2920
  Abstract | Full Text HTML | Hi-Res PDF

Letter

Amine-Promoted, Organocatalytic Aziridination of Enones

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Synthesis and Reactivity of C-Heteroatom-Substituted Aziridines

Asymmetric Synthesis of Diamine Derivatives via Sequential Palladium and Rhodium Catalysis

Enantioselective Catalytic Aziridinations and Asymmetric Nitrene Insertions into CH Bonds

Other ACS content by these authors:

JOURNALS

BOOKS

MAGAZINE

COMMUNITIES

DIRECTORIES & DATABASES