Literature DB >> 22233190

Rhodium(II)-catalyzed asymmetric sulfur(VI) reduction of diazo sulfonylamidines.

Nicklas Selander1, Valery V Fokin.   

Abstract

Diazo sulfonylamidines readily undergo enantioselective oxygen transfer from sulfur to carbon atom in the presence of chiral rhodium(II) carboxylates resulting in chiral sulfinylamidines. This unusual asymmetric atom transfer "reduction" occurs rapidly under mild conditions, and sulfinylamidines are obtained in excellent yield.

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Year:  2012        PMID： 22233190      PMCID： PMC3627535          DOI： 10.1021/ja210180q

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


  9 in total

1.  Recent developments in the synthesis and utilization of chiral sulfoxides.

Authors:  Inmaculada Fernández; Noureddine Khiar
Journal:  Chem Rev       Date:  2003-09       Impact factor: 60.622

2.  Catalytic asymmetric C-H insertions of rhodium(II) azavinyl carbenes.

Authors:  Stepan Chuprakov; Jamal A Malik; Mikhail Zibinsky; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2011-06-20       Impact factor: 15.419

3.  N-tert-butanesulfinyl imines: versatile intermediates for the asymmetric synthesis of amines.

Authors:  Jonathan A Ellman; Timothy D Owens; Tony P Tang
Journal:  Acc Chem Res       Date:  2002-11       Impact factor: 22.384

4.  Reactivity of N-(1,2,4-triazolyl)-substituted 1,2,3-triazoles.

Authors:  Mikhail Zibinsky; Valery V Fokin
Journal:  Org Lett       Date:  2011-08-18       Impact factor: 6.005

5.  Dirhodium tetracarboxylate derived from adamantylglycine as a chiral catalyst for carbenoid reactions.

Authors:  Ravisekhara P Reddy; Gene H Lee; Huw M L Davies
Journal:  Org Lett       Date:  2006-08-03       Impact factor: 6.005

6.  Synthesis and reactivity of rhodium(II) N-triflyl azavinyl carbenes.

Authors:  Neil Grimster; Li Zhang; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2010-03-03       Impact factor: 15.419

7.  Rhodium-catalyzed transannulation of 1,2,3-triazoles with nitriles.

Authors:  Tony Horneff; Stepan Chuprakov; Natalia Chernyak; Vladimir Gevorgyan; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2008-10-15       Impact factor: 15.419

8.  Rhodium-catalyzed enantioselective cyclopropanation of olefins with N-sulfonyl 1,2,3-triazoles.

Authors:  Stepan Chuprakov; Sen Wai Kwok; Li Zhang; Lukas Lercher; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2009-12-23       Impact factor: 15.419

9.  Selectivity enhancement in the Rh(II)-catalyzed cyclopropanation of styrene with (silanyloxyvinyl)diazoacetates.

Authors:  Paul Müller; Gérald Bernardinelli; Yves F Allenbach; Maria Ferri; Howard D Flack
Journal:  Org Lett       Date:  2004-05-27       Impact factor: 6.005
  9 in total
  7 in total

1.  Substrate-dependent divergent outcomes from catalytic reactions of silyl-protected enol diazoacetates with nitrile oxides: azabicyclo[3.1.0]hexanes or 5-arylaminofuran-2(3H)-ones.

Authors:  Xinfang Xu; Dmitry Shabashov; Peter Y Zavalij; Michael P Doyle
Journal:  J Org Chem       Date:  2012-06-04       Impact factor: 4.354

2.  Exploiting Configurational Lability in Aza-Sulfur Compounds for the Organocatalytic Enantioselective Synthesis of Sulfonimidamides.

Authors:  Michael J Tilby; Damien F Dewez; Adrian Hall; Carolina Martínez Lamenca; Michael C Willis
Journal:  Angew Chem Int Ed Engl       Date:  2021-11-02       Impact factor: 16.823

3.  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

4.  Transannulation of 1-sulfonyl-1,2,3-triazoles with heterocumulenes.

Authors:  Stepan Chuprakov; Sen Wai Kwok; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2013-03-15       Impact factor: 15.419

5.  Arylation of rhodium(II) azavinyl carbenes with boronic acids.

Authors:  Nicklas Selander; Brady T Worrell; Stepan Chuprakov; Subash Velaparthi; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2012-08-28       Impact factor: 15.419

6.  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

7.  Diversity-oriented synthesis of heterocycles and macrocycles by controlled reactions of oxetanes with α-iminocarbenes.

Authors:  Alejandro Guarnieri-Ibáñez; Florian Medina; Céline Besnard; Sarah L Kidd; David R Spring; Jérôme Lacour
Journal:  Chem Sci       Date:  2017-06-12       Impact factor: 9.825
  7 in total

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