Literature DB >> 20502818

A novel chiral oxazolidine organocatalyst for the synthesis of an oseltamivir intermediate using a highly enantioselective Diels-Alder reaction of 1,2-dihydropyridine.

Hiroto Nakano1, Kenichi Osone, Mitsuhiro Takeshita, Eunsang Kwon, Chigusa Seki, Haruo Matsuyama, Nobuhiro Takano, Yoshihito Kohari.   

Abstract

Enantioselective Diels-Alder reactions of 1,2-dihydropyridines with acroleins using a novel chiral oxazolidine organocatalyst afforded chiral isoquinuclidines that is an efficient synthetic intermediate of oseltamivir, with fairly good chemical yield and excellent enantioselectivity (90%, up to >99% ee).

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Year:  2010        PMID： 20502818     DOI： 10.1039/c0cc00110d

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  6 in total

1.  Synthesis of isoquinuclidines from highly substituted dihydropyridines via the Diels-Alder reaction.

Authors:  Rhia M Martin; Robert G Bergman; Jonathan A Ellman
Journal:  Org Lett       Date:  2013-01-15       Impact factor: 6.005

2.  2-Bromo-4-(3,4-dimethyl-5-phenyl-1,3-oxazolidin-2-yl)-6-meth-oxy-phenol.

Authors:  Maywan Hariono; Nurziana Ngah; Habibah A Wahab; Aisyah Saad Abdul Rahim
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-12-07

3.  Total synthesis of (+)-gelsemine via an organocatalytic Diels-Alder approach.

Authors:  Xiaoming Chen; Shengguo Duan; Cheng Tao; Hongbin Zhai; Fayang G Qiu
Journal:  Nat Commun       Date:  2015-05-21       Impact factor: 14.919

4.  Deeper Insight into the Six-Step Domino Reaction of Aldehydes with Malononitrile and Evaluation of Antiviral and Antimalarial Activities of the Obtained Bicyclic Products.

Authors:  Christina M Bock; Gangajji Parameshwarappa; Simon Bönisch; Walter Bauer; Corina Hutterer; Maria Leidenberger; Oliver Friedrich; Manfred Marschall; Barbara Kappes; Andreas Görling; Svetlana B Tsogoeva
Journal:  ChemistryOpen       Date:  2017-04-26       Impact factor: 2.911

5.  Stereoselective synthesis of isoquinuclidines through an aza-[4 + 2] cycloaddition of chiral cyclic 2-amidodienes.

Authors:  Li-Chao Fang; Richard P Hsung
Journal:  Org Lett       Date:  2014-03-12       Impact factor: 6.005

6.  Synthesis of spiro[indoline-3,1'-quinolizines] and spiro[indoline-3, 4'-pyrido[1,2-a]quinolines] via three-component reactions of azaarenes, acetylenedicarboxylate, and 3-methyleneoxindoles.

Authors:  Jing Sun; Hui Gong; Yan Sun; Chao-Guo Yan
Journal:  Mol Divers       Date:  2013-07-19       Impact factor: 2.943
  6 in total

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