Literature DB >> 16381556

Asymmetric synthesis of propargylamides via 3,3'-disubstituted binaphthol-modified alkynylboronates.

T Robert Wu1, J Michael Chong.   

Abstract

[reaction: see text] Alkynylboronates derived from 3,3'-disubstituted-2,2'-binaphthols react with various N-acylimines to give the expected chiral propargylamides with up to 99% ee. This new methodology was applied to the first enantioselective synthesis of the antitubulin agent (-)-N-acetylcolchinol.

Entities:  

Year:  2006        PMID: 16381556     DOI: 10.1021/ol0523087

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


  7 in total

1.  The Enantioselective Addition of Alkyne Nucleophiles to Carbonyl Groups.

Authors:  Barry M Trost; Andrew H Weiss
Journal:  Adv Synth Catal       Date:  2009-05       Impact factor: 5.837

2.  Central-to-Axial Chirality Transfer in the Benzannulation Reaction of Optically Pure Fischer Carbene Complexes in the Synthesis of Allocolchicinoids.

Authors:  Andrei V Vorogushin; William D Wulff; Hans-Jürgen Hansen
Journal:  Tetrahedron       Date:  2008-01-28       Impact factor: 2.457

3.  Enantioselective addition of boronates to o-quinone methides catalyzed by chiral biphenols.

Authors:  Yi Luan; Scott E Schaus
Journal:  J Am Chem Soc       Date:  2012-12-03       Impact factor: 15.419

4.  Boron carboxylate catalysis of homoallylboration.

Authors:  Gabrielle J Dugas; Yu-hong Lam; K N Houk; Isaac J Krauss
Journal:  J Org Chem       Date:  2014-04-24       Impact factor: 4.354

Review 5.  Gold-catalyzed cyclizations of alkynol-based compounds: synthesis of natural products and derivatives.

Authors:  Benito Alcaide; Pedro Almendros; José M Alonso
Journal:  Molecules       Date:  2011-09-13       Impact factor: 4.411

6.  Pyrinap ligands for enantioselective syntheses of amines.

Authors:  Qi Liu; Haibo Xu; Yuling Li; Yuan Yao; Xue Zhang; Yinlong Guo; Shengming Ma
Journal:  Nat Commun       Date:  2021-01-04       Impact factor: 14.919

7.  Direct Enantioselective Addition of Alkynes to Imines by a Highly Efficient Palladacycle Catalyst.

Authors:  Camilla Pfeffer; Patrick Probst; Nick Wannenmacher; Wolfgang Frey; René Peters
Journal:  Angew Chem Int Ed Engl       Date:  2022-07-19       Impact factor: 16.823

  7 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.