Literature DB >> 17439136

Highly enantioselective alpha-aminoxylation of aldehydes and ketones with a polymer-supported organocatalyst.

Daniel Font1, Amaia Bastero, Sonia Sayalero, Ciril Jimeno, Miquel A Pericàs.   

Abstract

The first catalytic enantioselective alpha-aminoxylation of aldehydes and ketones using an insoluble, polymer-supported organocatalyst (1) derived from trans-4-hydroxyproline is reported (ee: 96-99%). Reaction rates in the aminoxylation of cyclic ketones with 1 are higher than those reported with l-proline. The insoluble nature of 1 simplifies workup conditions and allows catalyst recycling without an apparent decrease in enantioselectivity or yield.

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Year:  2007        PMID： 17439136     DOI： 10.1021/ol070526p

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


  9 in total

1.  L-Proline Functionalized Polymers Prepared by RAFT Polymerization and Their Assemblies as Supported Organocatalysts.

Authors:  Annhelen Lu; Thomas P Smart; Thomas H Epps; Deborah A Longbottom; Rachel K O'Reilly
Journal:  Macromolecules       Date:  2011-09-27       Impact factor: 5.985

2.  Clickable polyglycerol hyperbranched polymers and their application to gold nanoparticles and acid-labile nanocarriers.

Authors:  Andrew Zill; Alexandra L Rutz; Richie E Kohman; Alaaldin M Alkilany; Catherine J Murphy; Hyunjoon Kong; Steven C Zimmerman
Journal:  Chem Commun (Camb)       Date:  2010-11-22       Impact factor: 6.222

3.  Organocatalyzed preparation of 1,4,5-trisubstituted-glycosyl-1,2,3-triazole derivatives.

Authors:  Monalisa Kundu; Ishani Bhaumik; Anup Kumar Misra
Journal:  Glycoconj J       Date:  2019-07-05       Impact factor: 2.916

4.  Continuous proline catalysis via leaching of solid proline.

Authors:  Suzanne M Opalka; Ashley R Longstreet; D Tyler McQuade
Journal:  Beilstein J Org Chem       Date:  2011-12-14       Impact factor: 2.883

5.  Continuous-flow enantioselective α-aminoxylation of aldehydes catalyzed by a polystyrene-immobilized hydroxyproline.

Authors:  Xacobe C Cambeiro; Rafael Martín-Rapún; Pedro O Miranda; Sonia Sayalero; Esther Alza; Patricia Llanes; Miquel A Pericàs
Journal:  Beilstein J Org Chem       Date:  2011-10-31       Impact factor: 2.883

6.  Ultrasound-promoted organocatalytic enamine-azide [3 + 2] cycloaddition reactions for the synthesis of ((arylselanyl)phenyl-1H-1,2,3-triazol-4-yl)ketones.

Authors:  Gabriel P Costa; Natália Seus; Juliano A Roehrs; Raquel G Jacob; Ricardo F Schumacher; Thiago Barcellos; Rafael Luque; Diego Alves
Journal:  Beilstein J Org Chem       Date:  2017-04-11       Impact factor: 2.883

Review 7.  Organocatalyzed asymmetric alpha-oxidation, alpha-aminoxylation and alpha-amination of carbonyl compounds.

Authors:  Tirayut Vilaivan; Worawan Bhanthumnavin
Journal:  Molecules       Date:  2010-02-11       Impact factor: 4.411

8.  Organocatalytic asymmetric nitroso aldol reaction of α-substituted malonamates.

Authors:  Ekta Gupta; Narendra Kumar Vaishanv; Sandeep Kumar; Raja Krishnan Purshottam; Ruchir Kant; Kishor Mohanan
Journal:  Beilstein J Org Chem       Date:  2022-02-21       Impact factor: 2.883

9.  Preparation of prolinamide with adamantane for aldol reaction catalysis in brine and separation using a poly(AN-MA-β-CD) nanofibrous film via host-guest interaction.

Authors:  Rui Wang; Enjie Xu; Zhenming Su; Haifeng Duan; Jinjin Wang; Longqi Xue; Yingjie Lin; Yaoxian Li; Zhonglin Wei; Qingbiao Yang
Journal:  RSC Adv       Date:  2018-08-07       Impact factor: 4.036
  9 in total

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