Literature DB >> 16144362

Iodomethylzinc phosphates: powerful reagents for the cyclopropanation of alkenes.

Marie-Christine Lacasse1, Cyril Poulard, André B Charette.   

Abstract

A new family of zinc carbenoids derived from phosphoric acids was developed and used in the cyclopropanation of allylic alcohols and ethers and also of unfunctionalized olefins. The use of the chiral phosphoric acid of a 3,3'-disubstituted BINOL leads to efficient stereocontrol, affording the cyclopropanes of allylic and homoallylic ethers with complete conversions and up to 93% ee. A catalytic version of this reaction using 10 mol % of the chiral phosphate reagent is also disclosed.

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Year:  2005        PMID： 16144362     DOI： 10.1021/ja0529687

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


  10 in total

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2.  Development and mechanism of an enantioselective bromocycloetherification reaction via Lewis base/chiral Brønsted acid cooperative catalysis.

Authors:  Scott E Denmark; Matthew T Burk
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3.  Nanocrystals perovskites photocatalyzed singlet oxygen generation for light-driven organic reactions.

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Review 4.  Axial preferences in allylation reactions via the Zimmerman-Traxler transition state.

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Journal:  Acc Chem Res       Date:  2013-05-14       Impact factor: 22.384

Review 5.  Ligand effects in homogeneous Au catalysis.

Authors:  David J Gorin; Benjamin D Sherry; F Dean Toste
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6.  Lithium BINOL phosphate catalyzed desymmetrization of meso-epoxides with aromatic thiols.

Authors:  Gajendrasingh Ingle; Michael G Mormino; Jon C Antilla
Journal:  Org Lett       Date:  2014-10-15       Impact factor: 6.005

7.  Mechanistic Studies of the TRIP-Catalyzed Allylation with Organozinc Reagents.

Authors:  Peter E Hartmann; Mattia Lazzarotto; Jakob Pletz; Stefan Tanda; Philipp Neu; Walter Goessler; Wolfgang Kroutil; A Daniel Boese; Michael Fuchs
Journal:  J Org Chem       Date:  2020-07-22       Impact factor: 4.354

8.  Bis[μ-bis-(2,6-diiso-propyl-phen-yl) phosphato-κ2 O:O']bis-[(2,2'-bi-pyridine-κ2 N,N')lithium] toluene disolvate and its catalytic activity in ring-opening polymerization of ∊-caprolactone and l-dilactide.

Authors:  Alexey E Kalugin; Pavel D Komarov; Mikhail E Minyaev; Konstantin A Lyssenko; Dmitrii M Roitershtein; Ilya E Nifant'ev
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2019-05-21

9.  Synthesis of Novel C/D Ring Modified Bile Acids.

Authors:  Roselis A Landaeta Aponte; Andreas Luxenburger; Scott A Cameron; Alex Weymouth-Wilson; Richard H Furneaux; Lawrence D Harris; Benjamin J Compton
Journal:  Molecules       Date:  2022-04-06       Impact factor: 4.411

10.  Radical asymmetric intramolecular α-cyclopropanation of aldehydes towards bicyclo[3.1.0]hexanes containing vicinal all-carbon quaternary stereocenters.

Authors:  Liu Ye; Qiang-Shuai Gu; Yu Tian; Xiang Meng; Guo-Cong Chen; Xin-Yuan Liu
Journal:  Nat Commun       Date:  2018-01-15       Impact factor: 14.919
  10 in total

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