Literature DB >> 26480953

Enantioselective Addition of a 2-Alkoxycarbonyl-1,3-dithiane to Imines Catalyzed by a Bis(guanidino)iminophosphorane Organosuperbase.

Azusa Kondoh1, Masafumi Oishi2, Tadahiro Takeda3, Masahiro Terada4,5.   

Abstract

A chiral bis(guanidino)iminophosphorane catalyzes enantioselective addition reactions of a 1,3-dithiane derivative as a pronucleophile. The chiral uncharged organosuperbase facilitates the addition of benzyloxycarbonyl-1,3-dithiane to aromatic N-Boc-protected imines to provide optically active α-amino-1,3-dithiane derivatives, which are valuable versatile building blocks in organic synthesis.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  1,3-dithianes; asymmetric catalysis; organocatalysis; organosuperbases; phosphazenes

Year:  2015        PMID: 26480953     DOI: 10.1002/anie.201508178

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  6 in total

Review 1.  Phosphine Organocatalysis.

Authors:  Hongchao Guo; Yi Chiao Fan; Zhanhu Sun; Yang Wu; Ohyun Kwon
Journal:  Chem Rev       Date:  2018-09-27       Impact factor: 60.622

2.  Phosphazene-catalyzed desymmetrization of cyclohexadienones by dithiane addition.

Authors:  Matthew A Horwitz; Elisabetta Massolo; Jeffrey S Johnson
Journal:  Beilstein J Org Chem       Date:  2017-04-24       Impact factor: 2.883

3.  Photoredox radical conjugate addition of dithiane-2-carboxylate promoted by an iridium(iii) phenyl-tetrazole complex: a formal radical methylation of Michael acceptors.

Authors:  Andrea Gualandi; Elia Matteucci; Filippo Monti; Andrea Baschieri; Nicola Armaroli; Letizia Sambri; Pier Giorgio Cozzi
Journal:  Chem Sci       Date:  2016-11-03       Impact factor: 9.825

4.  Enantioselective direct Mannich-type reactions of 2-benzylpyridine N-oxides catalyzed by chiral bis(guanidino)iminophosphorane organosuperbase.

Authors:  Qiupeng Hu; Azusa Kondoh; Masahiro Terada
Journal:  Chem Sci       Date:  2018-04-20       Impact factor: 9.825

5.  Bifunctional iminophosphorane catalysed enantioselective sulfa-Michael addition of alkyl thiols to alkenyl benzimidazoles.

Authors:  Michele Formica; Geoffroy Sorin; Alistair J M Farley; Jesús Díaz; Robert S Paton; Darren J Dixon
Journal:  Chem Sci       Date:  2018-07-23       Impact factor: 9.825

6.  BIMP-Catalyzed 1,3-Prototropic Shift for the Highly Enantioselective Synthesis of Conjugated Cyclohexenones.

Authors:  Jonathan C Golec; Eve M Carter; John W Ward; William G Whittingham; Luis Simón; Robert S Paton; Darren J Dixon
Journal:  Angew Chem Int Ed Engl       Date:  2020-08-07       Impact factor: 16.823

  6 in total

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