Literature DB >> 16925417

Enantioselective transfer aminoallylation: synthesis of optically active homoallylic primary amines.

Masaharu Sugiura1, Chieko Mori, Shu Kobayashi.   

Abstract

A camphorquinone-derived chiral homoallylic amine was found to react with various aldehydes via imine formation and asymmetric 2-azonia-Cope rearrangement to give optically active homoallylic primary amines. A practical level of enantioselectivity with high functional group tolerance has been attained in this transformation.

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Year:  2006        PMID: 16925417     DOI: 10.1021/ja064106r

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


  5 in total

1.  Synthesis and Biological Evaluation of Cremastrine and an Unnatural Analogue.

Authors:  Kristopher N Hahn; Olugbeminiyi O Fadeyi; Hyekyung P Cho; Craig W Lindsley
Journal:  Tetrahedron Lett       Date:  2012-05-10       Impact factor: 2.415

2.  Synthesis of quaternary α-methyl α-amino acids by asymmetric alkylation of pseudoephenamine alaninamide pivaldimine.

Authors:  Cedric L Hugelshofer; Kevin T Mellem; Andrew G Myers
Journal:  Org Lett       Date:  2013-06-07       Impact factor: 6.005

3.  Synergistic catalysis for cascade allylation and 2-aza-cope rearrangement of azomethine ylides.

Authors:  Liang Wei; Qiao Zhu; Lu Xiao; Hai-Yan Tao; Chun-Jiang Wang
Journal:  Nat Commun       Date:  2019-04-08       Impact factor: 14.919

4.  Lewis acidic FeCl3 promoted 2-aza-Cope rearrangement to afford α-substituted homoallylamines in dimethyl carbonate.

Authors:  Karthik Gadde; Jonas Daelemans; Bert U W Maes; Kourosch Abbaspour Tehrani
Journal:  RSC Adv       Date:  2019-06-07       Impact factor: 3.361

5.  Rigid and concave, 2,4-cis-substituted azetidine derivatives: A platform for asymmetric catalysis.

Authors:  Akina Yoshizawa; Antonio Feula; Louise Male; Andrew G Leach; John S Fossey
Journal:  Sci Rep       Date:  2018-04-25       Impact factor: 4.379

  5 in total

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