Literature DB >> 17025328

Aryl-substituted sulfonium betaines: preparation and use in the epoxidation of aldehydes.

David C Forbes1, Sejal R Amin, Christie J Bean, Michael C Standen.   

Abstract

Thermally induced decarboxylation of carboxymethylsulfonium betaines results in formation of the corresponding sulfur ylides in situ. Decarboxylation rates for a range of arylcarboxymethylsulfonium betaine salts have been determined using NMR spectroscopy, and the efficiency of ylide generation and trapping has been evaluated via methylidene transfer to a range of aldehydes to form epoxides.

Entities:  

Year:  2006        PMID： 17025328     DOI： 10.1021/jo061370u

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  5 in total

1.  Relative Stabilities of Transition States Determine Diastereocontrol in Sulfur Ylide Additions onto Chiral N-Sulfinyl Imines.

Authors:  E Alan Salter; David C Forbes; Andrzej Wierzbicki
Journal:  Int J Quantum Chem       Date:  2012-01-01       Impact factor: 2.444

2.  Synthesis of Chiral Aziridines through Decarboxylative Generation of Sulfur Ylides and their Reaction with Chiral Sulfinyl Imines.

Authors:  David C Forbes; Sampada V Bettigeri; Sejal R Amin; Christie J Bean; Amanda M Law; Robert A Stockman
Journal:  Synth Commun       Date:  2009-01-01       Impact factor: 2.007

3.  Sulfenylation Chemistry using Polymer-Supported Sulfides.

Authors:  David C Forbes; Sampada V Bettigeri; Nahla N Al-Azzeh; Brian P Finnigan; Joseph A Kundukulam
Journal:  Tetrahedron Lett       Date:  2009       Impact factor: 2.415

4.  Highly stereoselective methylene transfers onto butanediacetal-protected chiral non-racemic sulfinyl imines using S-ylide technology.

Authors:  David C Forbes; Sampada V Bettigeri; Susanna C Pischek
Journal:  Chem Commun (Camb)       Date:  2009-03-09       Impact factor: 6.222

5.  S-Methylidene Agents: Preparation of Chiral Non-Racemic Heterocycles.

Authors:  David C Forbes; Sampada V Bettigeri; Samit A Patrawala; Susanna C Pischek; Michael C Standen
Journal:  Tetrahedron       Date:  2009-01-03       Impact factor: 2.457
  5 in total

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