Literature DB >> 17628071

Stereoselective [2,3]-sigmatropic rearrangements of unstabilized nitrogen ylides.

Robert E Gawley1, Kwangyul Moon.   

Abstract

The steric course of the [2,3]-rearrangement of several unstabilized nitrogen ylides has been investigated. The reactions proceed cleanly through an anti transition state, affording modest to good yields of a single diastereomer of the product. In two examples containing an N-cinnamyl group, a competing [1,2]-rearrangement affords a minor product.

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Year:  2007        PMID： 17628071      PMCID： PMC2518686          DOI： 10.1021/ol071188v

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  5 in total

1.  Asymmetric [2,3]-rearrangement of glycine-derived allyl ammonium ylids.

Authors:  James A Workman; Neil P Garrido; Julien Sançon; Edward Roberts; Hans Peter Wessel; J B Sweeney
Journal:  J Am Chem Soc       Date:  2005-02-02       Impact factor: 15.419

2.  Competing Rearrangements of Ammonium Ylides: A Quantum Theoretical Study.

Authors:  George L. Heard; Brian F. Yates
Journal:  J Org Chem       Date:  1996-10-18       Impact factor: 4.354

3.  Tandem formation and [2,3] rearrangement of methylene ammonium ylides derived from amines and the Simmons-Smith reagent.

Authors:  Varinder K Aggarwal; Guang Yu Fang; Jonathan P H Charmant; Graham Meek
Journal:  Org Lett       Date:  2003-05-15       Impact factor: 6.005

4.  First efficient and general copper-catalyzed [2,3]-rearrangement of tetrahydropyridinium ylids.

Authors:  Edward Roberts; Julien P Sançon; Joseph B Sweeney; James A Workman
Journal:  Org Lett       Date:  2003-12-11       Impact factor: 6.005

5.  Ruthenium porphyrin catalyzed tandem sulfonium/ammonium ylide formation and [2,3]-sigmatropic rearrangement. A concise synthesis of (+/-)-platynecine.

Authors:  Cong-Ying Zhou; Wing-Yiu Yu; Philip Wai Hong Chan; Chi-Ming Che
Journal:  J Org Chem       Date:  2004-10-15       Impact factor: 4.354
  5 in total
  2 in total

1.  Dynamics and a unified understanding of competitive [2,3]- and [1,2]-sigmatropic rearrangements based on a study of ammonium ylides.

Authors:  Bibaswan Biswas; Sean C Collins; Daniel A Singleton
Journal:  J Am Chem Soc       Date:  2014-02-28       Impact factor: 15.419

2.  Tandem Palladium and Isothiourea Relay Catalysis: Enantioselective Synthesis of α-Amino Acid Derivatives via Allylic Amination and [2,3]-Sigmatropic Rearrangement.

Authors:  Stéphanie S M Spoehrle; Thomas H West; James E Taylor; Alexandra M Z Slawin; Andrew D Smith
Journal:  J Am Chem Soc       Date:  2017-08-22       Impact factor: 15.419
  2 in total

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