Literature DB >> 14531676

Catalytic asymmetric rearrangement of allylic trichloroacetimidates. A practical method for preparing allylic amines and congeners of high enantiomeric purity.

Carolyn E Anderson1, Larry E Overman.   

Abstract

COP-Cl catalyzes the rearrangement of (E)-allylic trichloroacetimidates to provide transposed allylic trichloroacetamides of high enantiopurity, a transformation that underlies the first truly practical method for transforming prochiral allylic alcohols to enantioenriched allylic amines and congeners. The high functional group compatibility of this asymmetric rearrangement and the demonstrated broad utility in synthesis of the allylic trichloroacetimidate to allylic trichloroacetamide conversion are singular features of this new catalytic asymmetric reaction.

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Year:  2003        PMID： 14531676     DOI： 10.1021/ja037086r

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


  30 in total

1.  An Efficient Synthesis of de novo Imidates via Aza-Claisen Rearrangements of N-Allyl Ynamides.

Authors:  Kyle A Dekorver; Troy D North; Richard P Hsung
Journal:  Synlett       Date:  2010-10       Impact factor: 2.454

2.  Design and synthesis of potential mechanism-based inhibitors of the aminotransferase BioA involved in biotin biosynthesis.

Authors:  Ce Shi; Courtney C Aldrich
Journal:  J Org Chem       Date:  2012-07-03       Impact factor: 4.354

3.  Molecular Rearrangements in the Construction of Complex Molecules.

Authors:  Larry E Overman
Journal:  Tetrahedron       Date:  2009-09-15       Impact factor: 2.457

4.  Palladium(II)-catalyzed enantioselective synthesis of 2-vinyl oxygen heterocycles.

Authors:  Jeffrey S Cannon; Angela C Olson; Larry E Overman; Nicole S Solomon
Journal:  J Org Chem       Date:  2012-02-08       Impact factor: 4.354

5.  Stereoselective Dynamic Cyclization of Allylic Azides: Synthesis of Tetralins, Chromanes, and Tetrahydroquinolines.

Authors:  Matthew R Porter; Rami M Shaker; Cristian Calcanas; Joseph J Topczewski
Journal:  J Am Chem Soc       Date:  2018-01-10       Impact factor: 15.419

6.  Mechanism-based inactivation by aromatization of the transaminase BioA involved in biotin biosynthesis in Mycobaterium tuberculosis.

Authors:  Ce Shi; Todd W Geders; Sae Woong Park; Daniel J Wilson; Helena I Boshoff; Orishadipe Abayomi; Clifton E Barry; Dirk Schnappinger; Barry C Finzel; Courtney C Aldrich
Journal:  J Am Chem Soc       Date:  2011-10-24       Impact factor: 15.419

7.  Catalytic asymmetric Claisen rearrangement of enolphosphonates: construction of vicinal tertiary and all-carbon quaternary centers.

Authors:  Jiajing Tan; Cheol-Hong Cheon; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2012-07-23       Impact factor: 15.336

8.  Formation and utility of azasilacyclopentadienes derived from silacyclopropenes and nitriles.

Authors:  Laura L Anderson; K A Woerpel
Journal:  Org Lett       Date:  2009-01-15       Impact factor: 6.005

9.  Asymmetric Synthesis of (+)-Iso-6-Cassine via Stereoselective Intramolecular Amidomercuration.

Authors:  Satwinder Singh; Om V Singh; Hyunsoo Han
Journal:  Tetrahedron Lett       Date:  2007-11-19       Impact factor: 2.415

10.  Promoter free allylation of trichloroacetimidates with allyltributylstannanes under thermal conditions to access the common 1,1'-diarylbutyl pharmacophore.

Authors:  Nivedita S Mahajani; John D Chisholm
Journal:  Org Biomol Chem       Date:  2018-05-30       Impact factor: 3.876
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