Literature DB >> 21116516

Cooperative catalysis in highly enantioselective Mannich-type three-component reaction of a diazoacetophenone with an alcohol and an imine.

Xinfang Xu1, Yu Qian, Liping Yang, Wenhao Hu.   

Abstract

A highly enantioselective three-component reaction of a diazoacetophenone, an alcohol, and an imine catalyzed cooperatively by Rh(2)(OAc)(4) and BINOL-derived chiral phosphoric acid has been developed for the synthesis of chiral β-amino-α-hydroxyl ketones in good yield with excellent diastereo and enantio selectivity.

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Year:  2010        PMID： 21116516     DOI： 10.1039/c0cc03024d

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


  5 in total

1.  Efficient synthesis of oxazoles by dirhodium(II)-catalyzed reactions of styryl diazoacetate with oximes.

Authors:  Xinfang Xu; Peter Y Zavalij; Wenhao Hu; Michael P Doyle
Journal:  Chem Commun (Camb)       Date:  2012-12-07       Impact factor: 6.222

2.  Dirhodium(II)-catalyzed formal [3+2+1]-annulation of azomethine imines with two molecules of a diazo ketone.

Authors:  Xinfang Xu; Xichen Xu; Peter Y Zavalij; Michael P Doyle
Journal:  Chem Commun (Camb)       Date:  2013-04-07       Impact factor: 6.222

3.  Vinylogous reactivity of enol diazoacetates with donor-acceptor substituted hydrazones. Synthesis of substituted pyrazole derivatives.

Authors:  Xinfang Xu; Peter Y Zavalij; Wenhao Hu; Michael P Doyle
Journal:  J Org Chem       Date:  2013-01-24       Impact factor: 4.354

4.  Brønsted acid catalysis - the effect of 3,3'-substituents on the structural space and the stabilization of imine/phosphoric acid complexes.

Authors:  Maxime Melikian; Johannes Gramüller; Johnny Hioe; Julian Greindl; Ruth M Gschwind
Journal:  Chem Sci       Date:  2019-04-08       Impact factor: 9.825

5.  Internal acidity scale and reactivity evaluation of chiral phosphoric acids with different 3,3'-substituents in Brønsted acid catalysis.

Authors:  Kerstin Rothermel; Maxime Melikian; Johnny Hioe; Julian Greindl; Johannes Gramüller; Matej Žabka; Nils Sorgenfrei; Thomas Hausler; Fabio Morana; Ruth M Gschwind
Journal:  Chem Sci       Date:  2019-09-06       Impact factor: 9.825
  5 in total

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