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Literature DB >> 31194906

Catalytic Enantioselective Synthesis of Allylic Boronates Bearing a Trisubstituted Alkenyl Fluoride and Related Derivatives.

Sota Akiyama¹, Koji Kubota^1,2, Malte S Mikus³, Paulo H S Paioti^3,4, Filippo Romiti^3,4, Qinghe Liu³, Yuebiao Zhou³, Amir H Hoveyda^3,4, Hajime Ito^1,2.

Abstract

The first catalytic method for diastereo- and enantioselective synthesis of allylic boronates bearing a Z-trisubstituted alkenyl fluoride is disclosed. Boryl substitution is performed with either a Z- or E-allyldifluoride and is catalyzed by bisphosphine/Cu complexes, affording products in up to 99 % yield with >98:2 Z/E selectivity and 99:1 enantiomeric ratio. A variety of subsequent modifications are feasible, and notable examples are diastereoselective additions to aldehydes/aldimines to access homoallylic alcohols/amines containing a fluorosubstituted stereogenic quaternary center.

Entities: Chemical Gene Mutation

Keywords: boron; copper; enantioselective catalysis; fluorine; synthetic methods

Year: 2019 PMID： 31194906 PMCID： PMC6707873 DOI： 10.1002/anie.201906283

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

34 in total

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3. NHC-Cu-catalyzed enantioselective hydroboration of acyclic and exocyclic 1,1-disubstituted aryl alkenes.

Authors: Rosa Corberán; Nicholas W Mszar; Amir H Hoveyda
Journal: Angew Chem Int Ed Engl Date: 2011-06-17 Impact factor: 15.336

4. Iridium-catalyzed allylic fluorination of trichloroacetimidates.

Authors: Joseph J Topczewski; Timothy J Tewson; Hien M Nguyen
Journal: J Am Chem Soc Date: 2011-11-11 Impact factor: 15.419

5. Enantioselective synthesis of allylboronates bearing a tertiary or quaternary B-substituted stereogenic carbon by NHC-Cu-catalyzed substitution reactions.

Authors: Aikomari Guzman-Martinez; Amir H Hoveyda
Journal: J Am Chem Soc Date: 2010-08-11 Impact factor: 15.419

Review 6. Fluorine & chirality: how to create a nonracemic stereogenic carbon-fluorine centre?

Authors: Dominique Cahard; Xiuhua Xu; Samuel Couve-Bonnaire; Xavier Pannecoucke
Journal: Chem Soc Rev Date: 2009-10-16 Impact factor: 54.564

7. Synthesis of β-fluoroamines by Lewis base catalyzed hydrofluorination of aziridines.

Authors: Julia A Kalow; Dana E Schmitt; Abigail G Doyle
Journal: J Org Chem Date: 2012-04-10 Impact factor: 4.354

8. Copper-catalyzed enantioselective substitution of allylic carbonates with diboron: an efficient route to optically active alpha-chiral allylboronates.

Authors: Hajime Ito; Shinichiro Ito; Yusuke Sasaki; Kou Matsuura; Masaya Sawamura
Journal: J Am Chem Soc Date: 2007-11-08 Impact factor: 15.419

Review 2. Beyond Carbon: Enantioselective and Enantiospecific Reactions with Catalytically Generated Boryl- and Silylcopper Intermediates.

Authors: Weichao Xue; Martin Oestreich
Journal: ACS Cent Sci Date: 2020-07-09 Impact factor: 14.553

Review 3. Recent Advances in the Construction of Fluorinated Organoboron Compounds.

Authors: Xingxing Ma; Zhijie Kuang; Qiuling Song
Journal: JACS Au Date: 2021-12-30

3 in total