Literature DB >> 15151399

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

Paul Müller1, Gérald Bernardinelli, Yves F Allenbach, Maria Ferri, Howard D Flack.   

Abstract

The cyclopropanation of styrene with (silanyloxyvinyl)diazoacetates proceeds with exceptional diastereo- and enantioselectivity in the presence of chiral Rh(II) catalysts. 1,8-Naphthoyl-protected amino acids are the most effective Rh(II) ligands for these transformations. [reaction--see text]

Entities:  

Year:  2004        PMID： 15151399     DOI： 10.1021/ol049554n

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


  14 in total

1.  Controlling factors for C-H functionalization versus cyclopropanation of dihydronaphthalenes.

Authors:  Etienne Nadeau; Dominic L Ventura; Jonathan A Brekan; Huw M L Davies
Journal:  J Org Chem       Date:  2010-03-19       Impact factor: 4.354

2.  Alkynoate synthesis through the vinylogous reactivity of rhodium(II) carbenoids.

Authors:  Damien Valette; Yajing Lian; John P Haydek; Kenneth I Hardcastle; Huw M L Davies
Journal:  Angew Chem Int Ed Engl       Date:  2012-07-16       Impact factor: 15.336

3.  Cobalt(II)-catalyzed asymmetric olefin cyclopropanation with α-ketodiazoacetates.

Authors:  Xue Xu; Shifa Zhu; Xin Cui; Lukasz Wojtas; X Peter Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2013-09-20       Impact factor: 15.336

4.  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

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

Authors:  Nicklas Selander; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2012-01-27       Impact factor: 15.419

6.  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

Review 7.  Cycloaddition reactions of enoldiazo compounds.

Authors:  Qing-Qing Cheng; Yongming Deng; Marianne Lankelma; Michael P Doyle
Journal:  Chem Soc Rev       Date:  2017-08-29       Impact factor: 54.564

8.  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

9.  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

10.  High Symmetry Dirhodium(II) Paddlewheel Complexes as Chiral Catalysts.

Authors:  Jørn Hansen; Huw M L Davies
Journal:  Coord Chem Rev       Date:  2008-03       Impact factor: 22.315
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