Literature DB >> 21218793

Highly enantioselective synthesis of tetrahydroquinolines via cobalt(II)-catalyzed tandem 1,5-hydride transfer/cyclization.

Weidi Cao1, Xiaohua Liu, Wentao Wang, Lili Lin, Xiaoming Feng.   

Abstract

A chiral catalyst prepared from N,N'-dioxide and Co(BF(4))(2)·6H(2)O was applied in the asymmetric hydride transfer initiated cyclization reaction, giving optically active tetrahydroquinolines in good yields with high enantioselectivities under mild reaction conditions. Meanwhile, in light of the absolute configuration of the product, a possible working model was proposed to explain the origin of the activation and asymmetric induction.

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Year:  2011        PMID: 21218793     DOI: 10.1021/ol1028282

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


  19 in total

1.  Facile Access to Ring-Fused Aminals via Direct α-Amination of Secondary Amines with ortho-Aminobenzaldehydes. Synthesis of Vasicine, Deoxyvasicine, Deoxyvasicinone, Mackinazolinone and Ruteacarpine.

Authors:  Matthew T Richers; Indubhusan Deb; Alena Yu Platonova; Chen Zhang; Daniel Seidel
Journal:  Synthesis (Stuttg)       Date:  2013-10-06       Impact factor: 3.157

2.  Redox-neutral α-C-H bond functionalization of secondary amines with concurrent C-P bond formation/N-alkylation.

Authors:  Deepankar Das; Daniel Seidel
Journal:  Org Lett       Date:  2013-08-19       Impact factor: 6.005

3.  C-H bond functionalization via hydride transfer: formation of α-arylated piperidines and 1,2,3,4-tetrahydroisoquinolines via stereoselective intramolecular amination of benzylic C-H bonds.

Authors:  Paul A Vadola; Ignacio Carrera; Dalibor Sames
Journal:  J Org Chem       Date:  2012-06-06       Impact factor: 4.354

4.  Redox-Neutral Aromatization of Cyclic Amines: Mechanistic Insights and Harnessing of Reactive Intermediates for Amine α- and β-C-H Functionalization.

Authors:  Longle Ma; Anirudra Paul; Martin Breugst; Daniel Seidel
Journal:  Chemistry       Date:  2016-11-09       Impact factor: 5.236

5.  Redox-neutral α-arylation of amines.

Authors:  Weijie Chen; Richard G Wilde; Daniel Seidel
Journal:  Org Lett       Date:  2013-12-13       Impact factor: 6.005

6.  Redox-neutral copper(II) carboxylate catalyzed α-alkynylation of amines.

Authors:  Deepankar Das; Aaron X Sun; Daniel Seidel
Journal:  Angew Chem Int Ed Engl       Date:  2013-02-25       Impact factor: 15.336

7.  Intramolecular Redox-Mannich Reactions: Facile Access to the Tetrahydroprotoberberine Core.

Authors:  Longle Ma; Daniel Seidel
Journal:  Chemistry       Date:  2015-07-28       Impact factor: 5.236

8.  Redox-neutral α,β-difunctionalization of cyclic amines.

Authors:  Weijie Chen; YoungKu Kang; Richard G Wilde; Daniel Seidel
Journal:  Angew Chem Int Ed Engl       Date:  2014-04-01       Impact factor: 15.336

9.  Metal-free α-amination of secondary amines: computational and experimental evidence for azaquinone methide and azomethine ylide intermediates.

Authors:  Arne Dieckmann; Matthew T Richers; Alena Yu Platonova; Chen Zhang; Daniel Seidel; K N Houk
Journal:  J Org Chem       Date:  2013-04-02       Impact factor: 4.354

10.  Asymmetric Redox-Annulation of Cyclic Amines.

Authors:  YoungKu Kang; Weijie Chen; Martin Breugst; Daniel Seidel
Journal:  J Org Chem       Date:  2015-10-02       Impact factor: 4.354

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