Literature DB >> 19928917

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

Stepan Chuprakov1, Sen Wai Kwok, Li Zhang, Lukas Lercher, Valery V Fokin.   

Abstract

N-Sulfonyl 1,2,3-triazoles readily form rhodium(II) azavinyl carbenes, which react with olefins to produce cyclopropanes with excellent diastereo- and enantioselectivity and in high yield.

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Year:  2009        PMID： 19928917      PMCID： PMC2801057          DOI： 10.1021/ja908075u

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


  21 in total

1.  Catalytic enantioselective C-H activation by means of metal-carbenoid-induced C-H insertion.

Authors:  Huw M L Davies; Rohan E J Beckwith
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

2.  Regiodivergent metal-catalyzed rearrangement of 3-iminocyclopropenes into N-fused heterocycles.

Authors:  Stepan Chuprakov; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2007-09-25       Impact factor: 6.005

3.  Rh-catalyzed transannulation of pyridotriazoles with alkynes and nitriles.

Authors:  Stepan Chuprakov; Frank W Hwang; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

4.  trans-Directing ability of amide groups in cyclopropanation: application to the asymmetric cyclopropanation of alkenes with diazo reagents bearing two carboxy groups.

Authors:  David Marcoux; André B Charette
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

5.  Catalytic asymmetric cyclopropanation of heteroaryldiazoacetates.

Authors:  H M Davies; R J Townsend
Journal:  J Org Chem       Date:  2001-10-05       Impact factor: 4.354

6.  Stereoselectivity of methyl aryldiazoacetate cyclopropanations of 1,1-diarylethylene. Asymmetric synthesis of a cyclopropyl analogue of tamoxifen.

Authors:  H M Davies; T Nagashima; J L Klino
Journal:  Org Lett       Date:  2000-03-23       Impact factor: 6.005

7.  Enantio- and diastereoselective synthesis of cis-2-aryl-3-methoxycarbonyl-2,3-dihydrobenzofurans via the Rh(II)-catalyzed C-H insertion process.

Authors:  Hiroaki Saito; Hiroyuki Oishi; Shinji Kitagaki; Seiichi Nakamura; Masahiro Anada; Shunichi Hashimoto
Journal:  Org Lett       Date:  2002-10-31       Impact factor: 6.005

8.  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

9.  Dirhodium(II) tetra(N-(dodecylbenzenesulfonyl)prolinate) catalyzed enantioselective cyclopropenation of alkynes.

Authors:  Huw M L Davies; Gene H Lee
Journal:  Org Lett       Date:  2004-04-15       Impact factor: 6.005

Review 10.  Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion.

Authors:  Huw M L Davies; James R Manning
Journal:  Nature       Date:  2008-01-24       Impact factor: 49.962
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  39 in total

1.  Synthesis and reactivity of sulfamoyl azides and 1-sulfamoyl-1,2,3-triazoles.

Authors:  Jeffrey C Culhane; Valery V Fokin
Journal:  Org Lett       Date:  2011-08-03       Impact factor: 6.005

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.  Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines.

Authors:  John M Bennett; Jonathan D Shapiro; Krystina N Choinski; Yingbin Mei; Sky M Aulita; Giovanny M Dominguez; Max M Majireck
Journal:  J Vis Exp       Date:  2018-01-03       Impact factor: 1.355

4.  Rhodium-Catalyzed Intermolecular C-H Functionalization as a Key Step in the Synthesis of Complex Stereodefined β-Arylpyrrolidines.

Authors:  Robert W Kubiak; Huw M L Davies
Journal:  Org Lett       Date:  2018-06-21       Impact factor: 6.005

5.  Versatile reactivity of rhodium-iminocarbenes derived from N-sulfonyl triazoles.

Authors:  Anton V Gulevich; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2013-01-07       Impact factor: 15.336

6.  Ring expansion and rearrangements of rhodium(II) azavinyl carbenes.

Authors:  Nicklas Selander; Brady T Worrell; Valery V Fokin
Journal:  Angew Chem Int Ed Engl       Date:  2012-11-19       Impact factor: 15.336

7.  Stereoconvergent [1,2]- and [1,4]-Wittig rearrangements of 2-silyl-6-aryl-5,6-dihydropyrans: a tale of steric vs electronic regiocontrol of divergent pathways.

Authors:  Luis M Mori-Quiroz; Robert E Maleczka
Journal:  J Org Chem       Date:  2015-01-16       Impact factor: 4.354

8.  Stereoselective 1,3-insertions of rhodium(II) azavinyl carbenes.

Authors:  Stepan Chuprakov; Brady T Worrell; Nicklas Selander; Rakesh K Sit; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2013-12-17       Impact factor: 15.419

9.  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

10.  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
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