Literature DB >> 17552531

Enantioselective synthesis of trifluoromethyl-substituted cyclopropanes.

Justin R Denton1, Dinesh Sukumaran, Huw M L Davies.   

Abstract

The reaction of 1-aryl-2,2,2-trifluorodiazoethanes with alkenes, catalyzed by the adamantylglycine-derived dirhodium complex Rh2(R-PTAD)4, generates trifluoromethyl-substituted cyclopropanes with high diastereoselectivity (>94%) and enantioselectivity (88->98%).

Entities:  

Year:  2007        PMID： 17552531     DOI： 10.1021/ol070714f

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


  14 in total

1.  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

2.  A coupling of benzamides and donor/acceptor diazo compounds to form γ-lactams via Rh(III)-catalyzed C-H activation.

Authors:  Todd K Hyster; Kyle E Ruhl; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2013-04-02       Impact factor: 15.419

3.  Enantioselective Formation of CF3-Bearing All-Carbon Quaternary Stereocenters via C-H Functionalization of Methanol: Iridium Catalyzed Allene Hydrohydroxymethylation.

Authors:  Michael Holmes; Khoa D Nguyen; Leyah A Schwartz; Tom Luong; Michael J Krische
Journal:  J Am Chem Soc       Date:  2017-06-12       Impact factor: 15.419

4.  Rhodium-catalyzed enantioselective cyclopropanation of electron deficient alkenes.

Authors:  Hengbin Wang; David M Guptill; Adrian Varela Alvarez; Djamaladdin G Musaev; Huw M L Davies
Journal:  Chem Sci       Date:  2013-07       Impact factor: 9.825

5.  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

6.  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

7.  Finding Opportunities from Surprises and Failures. Development of Rhodium-Stabilized Donor/Acceptor Carbenes and Their Application to Catalyst-Controlled C-H Functionalization.

Authors:  Huw M L Davies
Journal:  J Org Chem       Date:  2019-10-10       Impact factor: 4.354

8.  Guide to Enantioselective Dirhodium(II)-Catalyzed Cyclopropanation with Aryldiazoacetates.

Authors:  Kathryn M Chepiga; Changming Qin; Joshua S Alford; Spandan Chennamadhavuni; Timothy M Gregg; Jeremy P Olson; Huw M L Davies
Journal:  Tetrahedron       Date:  2013-07-08       Impact factor: 2.457

9.  Cross-dehydrogenative coupling enables enantioselective access to CF3-substituted all-carbon quaternary stereocenters.

Authors:  Xiaoguang Pan; Zehua Wang; Linglong Kan; Ying Mao; Yasheng Zhu; Lei Liu
Journal:  Chem Sci       Date:  2020-01-29       Impact factor: 9.825

10.  Flow chemistry as a discovery tool to access sp2-sp3 cross-coupling reactions via diazo compounds.

Authors:  Duc N Tran; Claudio Battilocchio; Shing-Bong Lou; Joel M Hawkins; Steven V Ley
Journal:  Chem Sci       Date:  2014-11-07       Impact factor: 9.825
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