Literature DB >> 19146454

Enantioselective reactions of donor/acceptor carbenoids derived from alpha-aryl-alpha-diazoketones.

Justin R Denton1, Huw M L Davies.   

Abstract

The reaction of a variety of alpha-aryl-alpha-diazo ketones with activated olefins, catalyzed by the adamantyl glycine-derived dirhodium complex Rh(2)(S-PTAD)(4), generates cyclopropyl ketones with high diastereoselectivity (up to >95:5 dr) and enantioselectivity (up to 98% ee). Intermolecular C-H functionalization of 1,4-cyclohexadiene by means of carbenoid-induced C-H insertion was also possible with this type of carbenoid.

Entities:  

Year:  2009        PMID： 19146454     DOI： 10.1021/ol802614j

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


  15 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.  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.  Catalytic Enantio- and Diastereoselective Cyclopropanation of 2-Azadienes for the Synthesis of Aminocyclopropanes Bearing Quaternary Carbon Stereogenic Centers.

Authors:  Xinxin Shao; Steven J Malcolmson
Journal:  Org Lett       Date:  2019-08-29       Impact factor: 6.005

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.  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

7.  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

8.  A Diverse Library of Chiral Cyclopropane Scaffolds via Chemoenzymatic Assembly and Diversification of Cyclopropyl Ketones.

Authors:  Donggeon Nam; Viktoria Steck; Robert J Potenzino; Rudi Fasan
Journal:  J Am Chem Soc       Date:  2021-01-26       Impact factor: 15.419

9.  Beyond Iron: Iridium-Containing P450 Enzymes for Selective Cyclopropanations of Structurally Diverse Alkenes.

Authors:  Hanna M Key; Paweł Dydio; Zhennan Liu; Jennifer Y-E Rha; Andrew Nazarenko; Vida Seyedkazemi; Douglas S Clark; John F Hartwig
Journal:  ACS Cent Sci       Date:  2017-04-01       Impact factor: 14.553

10.  Streamlined asymmetric α-difunctionalization of ynones.

Authors:  Siyu Peng; Zhaofeng Wang; Linxing Zhang; Xinhao Zhang; Yong Huang
Journal:  Nat Commun       Date:  2018-01-25       Impact factor: 14.919
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