Literature DB >> 25390507

Efficient and highly enantioselective construction of trifluoromethylated quaternary stereogenic centers via high-pressure mediated organocatalytic conjugate addition of nitromethane to β,β-disubstituted enones.

Piotr Kwiatkowski1, Agnieszka Cholewiak, Adrian Kasztelan.   

Abstract

A very effective high-pressure-induced acceleration of asymmetric organocatalytic conjugate addition of nitromethane to sterically congested β,β-disubstituted β-CF3 enones has been developed. A combination of pressure (8-10 kbar) and noncovalent catalysis with low-loading of chiral tertiary amine-thioureas (0.5-3 mol %) is shown to provide very efficient access to a wide range of γ-nitroketones containing trifluoromethylated all-carbon quaternary stereogenic centers in the β-position (80-97%, 92-98% ee).

Entities:  

Year:  2014        PMID: 25390507     DOI: 10.1021/ol502941d

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


  7 in total

1.  Enantio- and Diastereoselective Organocatalytic Conjugate Additions of Nitroalkanes to Enone Diesters.

Authors:  Matthew A Horwitz; Jennifer L Fulton; Jeffrey S Johnson
Journal:  Org Lett       Date:  2017-11-03       Impact factor: 6.005

2.  Enantioselective Formation of CF3-Bearing All-Carbon Quaternary Stereocenters via C-H Functionalization of Methanol: Iridium Catalyzed Allene Hydrohydroxymethylation.

Authors:  Michael Holmes; Khoa D Nguyen; Leyah A Schwartz; Tom Luong; Michael J Krische
Journal:  J Am Chem Soc       Date:  2017-06-12       Impact factor: 15.419

3.  Cross-dehydrogenative coupling enables enantioselective access to CF3-substituted all-carbon quaternary stereocenters.

Authors:  Xiaoguang Pan; Zehua Wang; Linglong Kan; Ying Mao; Yasheng Zhu; Lei Liu
Journal:  Chem Sci       Date:  2020-01-29       Impact factor: 9.825

4.  Efficient Synthesis of β-CF3/SCF3-Substituted Carbonyls via Copper-Catalyzed Electrophilic Ring-Opening Cross-Coupling of Cyclopropanols.

Authors:  Yong Li; Zhishi Ye; Tabitha M Bellman; Teng Chi; Mingji Dai
Journal:  Org Lett       Date:  2015-04-17       Impact factor: 6.072

5.  Copper(II)-Dioxygen Facilitated Activation of Nitromethane: Nitrogen Donors for the Synthesis of Substituted 2-Hydroxyimino-2-phenylacetonitriles and Phthalimides.

Authors:  Shiqun Xiang; Yinghua Li; Weibin Fan; Jiang Jin; Wei Zhang; Deguang Huang
Journal:  Front Chem       Date:  2021-01-29       Impact factor: 5.221

6.  Organocatalytic asymmetric Michael/acyl transfer reaction between α-nitroketones and 4-arylidenepyrrolidine-2,3-diones.

Authors:  Chandrakanta Parida; Subhas Chandra Pan
Journal:  Beilstein J Org Chem       Date:  2021-06-14       Impact factor: 2.883

Review 7.  Chiral Thioureas-Preparation and Significance in Asymmetric Synthesis and Medicinal Chemistry.

Authors:  Franz Steppeler; Dominika Iwan; Elżbieta Wojaczyńska; Jacek Wojaczyński
Journal:  Molecules       Date:  2020-01-18       Impact factor: 4.411

  7 in total

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