Literature DB >> 24251986

Silica-immobilized chiral dirhodium(II) catalyst for enantioselective carbenoid reactions.

Kathryn M Chepiga1, Yan Feng, Nicholas A Brunelli, Christopher W Jones, Huw M L Davies.   

Abstract

A silica-supported dirhodium(II) tetraprolinate catalyst was synthesized in four steps from l-proline and used in a range of enantioselective transformations of donor/acceptor carbenoids. These include cyclopropenation, cyclopropanation, tandem ylide formation/[2,3] sigmatropic rearrangement, and a variety of combined C-H functionalization/Cope rearrangement reactions. The products of these transformations were obtained in yields and levels of enantioselectivity comparable to those obtained with its homogeneous counterpart, Rh2(S-DOSP)4. The silica-supported Rh2(S-DOSP)4 derivative was successfully recycled over five reactions.

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Year:  2013        PMID： 24251986     DOI： 10.1021/ol403006r

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


  12 in total

1.  Silica-Supported Oligomeric Benzyl Phosphate (Si-OBP) and Triazole Phosphate (Si-OTP) Alkylating Reagents.

Authors:  Pradip K Maity; Saqib Faisal; Alan Rolfe; Diana Stoianova; Paul R Hanson
Journal:  J Org Chem       Date:  2015-10-02       Impact factor: 4.354

2.  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

3.  Chemiluminescence-promoted oxidation of alkyl enol ethers by NHPI under mild conditions and in the dark.

Authors:  T E Anderson; Alexander A Andia; K A Woerpel
Journal:  Tetrahedron       Date:  2020-12-24       Impact factor: 2.457

4.  Synthesis of High-Load, Hybrid Silica-Immobilized Heterocyclic Benzyl Phosphate (Si-OHBP) and Triazolyl Phosphate (Si-OHTP) Alkylating Reagents.

Authors:  Saqib Faisal; Pradip K Maity; Qin Zang; Alan Rolfe; Paul R Hanson
Journal:  ACS Comb Sci       Date:  2016-06-14       Impact factor: 3.784

5.  Application of Silica-Supported Alkylating Reagents in a One-Pot, Sequential Protocol to Diverse Benzoxathiazepine 1,1-Dioxides.

Authors:  Saqib Faisal; Pradip K Maity; Qin Zang; Thiwanka B Samarakoon; Robert L Sourk; Paul R Hanson
Journal:  ACS Comb Sci       Date:  2016-06-14       Impact factor: 3.784

6.  A fully recyclable heterogenized Cu catalyst for the general carbene transfer reaction in batch and flow.

Authors:  Lourdes Maestre; Erhan Ozkal; Carles Ayats; Álvaro Beltrán; M Mar Díaz-Requejo; Pedro J Pérez; Miquel A Pericàs
Journal:  Chem Sci       Date:  2014-11-28       Impact factor: 9.825

7.  Catalytic Synthesis of Trifluoromethyl Cyclopropenes and Oligo-Cyclopropenes.

Authors:  Uyen P N Tran; Renè Hommelsheim; Zhen Yang; Claire Empel; Katharina J Hock; Thanh V Nguyen; René M Koenigs
Journal:  Chemistry       Date:  2020-01-20       Impact factor: 5.236

Review 8.  Enantioselective carbenoid insertion into C(sp(3))-H bonds.

Authors:  J V Santiago; A H L Machado
Journal:  Beilstein J Org Chem       Date:  2016-05-04       Impact factor: 2.883

9.  Recyclable heterogeneous metal foil-catalyzed cyclopropenation of alkynes and diazoacetates under solvent-free mechanochemical reaction conditions.

Authors:  Longrui Chen; Devonna Leslie; Michael G Coleman; James Mack
Journal:  Chem Sci       Date:  2018-04-24       Impact factor: 9.825

10.  Photoinduced Heterogeneous C-H Arylation by a Reusable Hybrid Copper Catalyst.

Authors:  Isaac Choi; Valentin Müller; Gaurav Lole; Robert Köhler; Volker Karius; Wolfgang Viöl; Christian Jooss; Lutz Ackermann
Journal:  Chemistry       Date:  2020-02-25       Impact factor: 5.236
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