Literature DB >> 15984846

Asymmetric [2,3]-sigmatropic rearrangement of allylic ammonium ylides.

Jan Blid1, Olaf Panknin, Peter Somfai.   

Abstract

An asymmetric Lewis acid-mediated [2,3]-sigmatropic rearrangement of allylic amines has been developed, affording the corresponding homoallylic amines in good yield and excellent enantioselectivities. The rearrangement proceeds by complexation of the chiral Lewis acid to the amine followed by deprotonation and rearrangement.

Entities:  

Year:  2005        PMID： 15984846     DOI： 10.1021/ja0510562

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  3 in total

1.  Further studies on vinamidinium salt amine exchange reactions, borohydride reductions and subsequent transformations.

Authors:  John T Gupton; Nakul Telang; Xin Jia; Benjamin C Giglio; James E Eaton; Peter J Barelli; Mona Hovaizi; Kayleigh E Hall; R Scott Welden; Matthew J Keough; Eric F Worrall; Kara L Finzel; Emily J Kluball; Rene P F Kanters; Timothy M Smith; Stanton Q Smith; Shane R Nunes; Mathew T Wright; Jennifer M Birnstihl
Journal:  Tetrahedron       Date:  2010-10-30       Impact factor: 2.457

2.  Catalytic Enantioselective [2,3]-Rearrangements of Allylic Ammonium Ylides: A Mechanistic and Computational Study.

Authors:  Thomas H West; Daniel M Walden; James E Taylor; Alexander C Brueckner; Ryne C Johnston; Paul Ha-Yeon Cheong; Guy C Lloyd-Jones; Andrew D Smith
Journal:  J Am Chem Soc       Date:  2017-03-10       Impact factor: 15.419

3.  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
  3 in total

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