Prev. Article Next Article Table of Contents

Letter

One-Carbon Homologation of N-Sulfonylaziridines to Allylic Amines Using Dimethylsulfonium Methylide

Supporting Info

David M. Hodgson,* Matthew J. Fleming, and Steven J. Stanway^†

Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK

Org. Lett., 2005, 7 (15), pp 3295–3298

DOI: 10.1021/ol051124p

Publication Date (Web): June 21, 2005

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

†

GlaxoSmithKline, New Frontiers Science Park, Third Avenue, Harlow, Essex CM19 5AW, UK.

, david.hodgson@chem.ox.ac.uk

Abstract

Regio- and stereodefined allylic N-sulfonylamines are synthesized in high yields and under experimentally straightforward conditions by reaction of N-sulfonylaziridines with excess dimethylsulfonium methylide.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue July 21, 2005
Received May 14, 2005

Recommend & Share

Related Content

Substituted Aziridines by Lithiation−Electrophile Trapping of Terminal AziridinesOrganic Letters
- Substituted Aziridines by Lithiation−Electrophile Trapping of Terminal Aziridines
  David M. Hodgson, Philip G. Humphreys, and John G. Ward
  Organic Letters 2005 7 (6), pp 1153–1156
  Abstract: Regio- and stereoselective deprotonation of N-Bus (Bus = tert-butylsulfonyl)-protected terminal aziridines with lithium 2,2,6,6-tetramethylpiperidide generates a nonstabilized (H-substituted) aziridinyl anion that undergoes in situ or external ...
  Abstract | Full Text HTML | Hi-Res PDF
Efficient Aziridination of Olefins Catalyzed by Mixed-Valent Dirhodium(II,III) CaprolactamateOrganic Letters
- Efficient Aziridination of Olefins Catalyzed by Mixed-Valent Dirhodium(II,III) Caprolactamate
  Arthur J. Catino, Jason M. Nichols, Raymond E. Forslund, and Michael P. Doyle
  Organic Letters 2005 7 (13), pp 2787–2790
  Abstract: A mild, efficient, and selective aziridination of olefins catalyzed by dirhodium(II) caprolactamate [Rh₂(cap)₄·2CH₃CN] is described. Use of p-toluenesulfonamide (TsNH₂), N-bromosuccinimide (NBS), and potassium carbonate readily affords aziridines in ...
  Abstract | Full Text HTML | Hi-Res PDF
Lewis Base Catalyzed Ring Opening of Aziridines with Silylated NucleophilesOrganic Letters
- Lewis Base Catalyzed Ring Opening of Aziridines with Silylated Nucleophiles
  Satoshi Minakata, Yuriko Okada, Yoji Oderaotoshi, and Mitsuo Komatsu
  Organic Letters 2005 7 (16), pp 3509–3512
  Abstract: The ring opening of N-tosylaziridines with trimethylsilylated nucleophiles, catalyzed by N,N,N‘,N‘-tetramethylethylenediamine, led to the production of β-functionalized sulfonamides in good to excellent yields with high regioselectivity.
  Abstract | Full Text HTML | Hi-Res PDF

Letter

One-Carbon Homologation of N-Sulfonylaziridines to Allylic Amines Using Dimethylsulfonium Methylide

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Substituted Aziridines by Lithiation−Electrophile Trapping of Terminal Aziridines

Efficient Aziridination of Olefins Catalyzed by Mixed-Valent Dirhodium(II,III) Caprolactamate

Lewis Base Catalyzed Ring Opening of Aziridines with Silylated Nucleophiles

Other ACS content by these authors:

JOURNALS

BOOKS

MAGAZINE

COMMUNITIES

DIRECTORIES & DATABASES