Literature DB >> 15898758

Catalytic and asymmetric vinylogous mukaiyama reactions on aliphatic ketones: formal asymmetric synthesis of taurospongin a.

Xavier Moreau1, Belen Bazán-Tejeda, Jean-Marc Campagne.   

Abstract

Catalytic asymmetric vinylogous Mukaiyama reactions on ketones, leading to the formation of alpha,beta-unsaturated lactones with tertiary alcohols, have been described (11 examples, up to 93% ee). This methodology has been applied in a formal enantioselective synthesis of taurospongin A (12 steps, 6% overall yield).

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Year:  2005        PMID： 15898758     DOI： 10.1021/ja051573k

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


  6 in total

1.  Chiral imine copper chloride-catalyzed enantioselective desymmetrization of 2-substituted 1,2,3-propanetriols.

Authors:  Byunghyuck Jung; Sung Ho Kang
Journal:  Proc Natl Acad Sci U S A       Date:  2007-01-22       Impact factor: 11.205

2.  Enantioselective iridium-catalyzed vinylogous Reformatsky-aldol reaction from the alcohol oxidation level: linear regioselectivity by way of carbon-bound enolates.

Authors:  Abbas Hassan; Jason R Zbieg; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2011-03-04       Impact factor: 15.336

3.  Biologically active Phytophthora mating hormone prepared by catalytic asymmetric total synthesis.

Authors:  Syuzanna R Harutyunyan; Zhijian Zhao; Tim den Hartog; Klaas Bouwmeester; Adriaan J Minnaard; Ben L Feringa; Francine Govers
Journal:  Proc Natl Acad Sci U S A       Date:  2008-06-16       Impact factor: 11.205

Review 4.  Chiral poly-rare earth metal complexes in asymmetric catalysis.

Authors:  Masakatsu Shibasaki
Journal:  Proc Jpn Acad Ser B Phys Biol Sci       Date:  2006-04       Impact factor: 3.493

5.  Direct catalytic enantio- and diastereoselective ketone aldol reactions of isocyanoacetates.

Authors:  Raquel de la Campa; Irene Ortín; Darren J Dixon
Journal:  Angew Chem Int Ed Engl       Date:  2015-03-03       Impact factor: 15.336

6.  Activation of allylic esters in an intramolecular vinylogous kinetic resolution reaction with synergistic magnesium catalysts.

Authors:  Dan Li; Yuling Yang; Minmin Zhang; Linqing Wang; Yingfan Xu; Dongxu Yang; Rui Wang
Journal:  Nat Commun       Date:  2020-05-22       Impact factor: 14.919
  6 in total

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