Literature DB >> 24910778

Stereoselective Intramolecular Cyclopropanation of α-Diazoacetates via Co(II)-Based Metalloradical Catalysis.

Joshua V Ruppel, Xin Cui, Xue Xu, X Peter Zhang.   

Abstract

Co(II) complexes of D2-symmetric chiral porphyrins have been proven to be effective metalloradical catalysts for the asymmetric intramolecular cyclopropanation of allyl α-diazoacetates. 4-(Dimethylamino)pyridine (DMAP), through positive trans effect, plays an important role in the enhancement of the asymmetric induction for the intramolecular cyclopropanation process. This metalloradical catalytic system is suitable for cyclopropanation of allyl α-diazoacetates with varied functional groups and substitution patterns, producing bicyclic products with complete diastereocontrol and good enantiocontrol.

Entities:  

Year:  2014        PMID： 24910778      PMCID： PMC4043383          DOI： 10.1039/C4QO00041B

Source DB:  PubMed          Journal:  Org Chem Front        ISSN： 2052-4110            Impact factor:   5.281


  22 in total

Review 1.  Biosynthesis and metabolism of cyclopropane rings in natural compounds.

Authors:  Ludger A Wessjohann; Wolfgang Brandt; Thies Thiemann
Journal:  Chem Rev       Date:  2003-04       Impact factor: 60.622

2.  Chiral bis(oxazolinyl)phenyl Ru(II) catalysts for highly enantioselective cyclopropanation.

Authors:  Jun-ichi Ito; Satoshi Ujiie; Hisao Nishiyama
Journal:  Chemistry       Date:  2010-05-03       Impact factor: 5.236

3.  Transition metal chemistry of cyclopropenes and cyclopropanes.

Authors:  Michael Rubin; Marina Rubina; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2007-07       Impact factor: 60.622

Review 4.  Heterocycles from cyclopropanes: applications in natural product synthesis.

Authors:  Cheryl A Carson; Michael A Kerr
Journal:  Chem Soc Rev       Date:  2009-07-10       Impact factor: 54.564

5.  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

6.  Asymmetric inter- and intramolecular cyclopropanation of alkenes catalyzed by chiral ruthenium porphyrins. Synthesis and crystal structure of a chiral metalloporphyrin carbene complex.

Authors:  C M Che; J S Huang; F W Lee; Y Li; T S Lai; H L Kwong; P F Teng; W S Lee; W C Lo; S M Peng; Z Y Zhou
Journal:  J Am Chem Soc       Date:  2001-05-09       Impact factor: 15.419

7.  Comparative enantiocontrol with allyl phenyldiazoacetates in asymmetric catalytic intramolecular cyclopropanation.

Authors:  Michael P Doyle; Wenhao Hu; Thomas M Weathers
Journal:  Chirality       Date:  2003-05-05       Impact factor: 2.437

8.  Amplification of asymmetric induction in sequential reactions of bis-diazoacetates catalyzed by chiral dirhodium(II) carboxamidates.

Authors:  Michael P Doyle; Yuanhua Wang; Pejman Ghorbani; Erhard Bappert
Journal:  Org Lett       Date:  2005-10-27       Impact factor: 6.005

9.  Cobalt-catalyzed asymmetric cyclopropanation with diazosulfones: rigidification and polarization of ligand chiral environment via hydrogen bonding and cyclization.

Authors:  Shifa Zhu; Joshua V Ruppel; Hongjian Lu; Lukasz Wojtas; X Peter Zhang
Journal:  J Am Chem Soc       Date:  2008-03-22       Impact factor: 15.419

10.  Asymmetric cyclopropanation of styrenes catalyzed by metal complexes of D2-symmetrical chiral porphyrin: superiority of cobalt over iron.

Authors:  Ying Chen; X Peter Zhang
Journal:  J Org Chem       Date:  2007-06-23       Impact factor: 4.354
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  4 in total

Review 1.  Transition Metal Catalysis Controlled by Hydrogen Bonding in the Second Coordination Sphere.

Authors:  Joost N H Reek; Bas de Bruin; Sonja Pullen; Tiddo J Mooibroek; Alexander M Kluwer; Xavier Caumes
Journal:  Chem Rev       Date:  2022-05-20       Impact factor: 72.087

2.  Cobalt(II)-tetraphenylporphyrin-catalysed carbene transfer from acceptor-acceptor iodonium ylides via N-enolate-carbene radicals.

Authors:  Roel F J Epping; Mees M Hoeksma; Eduard O Bobylev; Simon Mathew; Bas de Bruin
Journal:  Nat Chem       Date:  2022-03-24       Impact factor: 24.274

Review 3.  Carbene Transfer Reactions Catalysed by Dyes of the Metalloporphyrin Group.

Authors:  Mário M Q Simões; Daniel T G Gonzaga; Mariana F C Cardoso; Luana da S M Forezi; Ana T P C Gomes; Fernando de C da Silva; Vítor F Ferreira; Maria G P M S Neves; José A S Cavaleiro
Journal:  Molecules       Date:  2018-03-29       Impact factor: 4.411

4.  Revisiting the Electronic Structure of Cobalt Porphyrin Nitrene and Carbene Radicals with NEVPT2-CASSCF Calculations: Doublet versus Quartet Ground States.

Authors:  Nicolaas P van Leest; Bas de Bruin
Journal:  Inorg Chem       Date:  2021-06-05       Impact factor: 5.165
  4 in total

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