Literature DB >> 27159674

Enantioselective Synthesis of Cyclobutylboronates via a Copper-Catalyzed Desymmetrization Approach.

Manuel Guisán-Ceinos1, Alejandro Parra1, Víctor Martín-Heras1, Mariola Tortosa2.   

Abstract

The first catalytic enantioselective synthesis of cyclobutylboronates, by using a chiral copper(I) complex, is reported. A broad variety of cyclobutanes have been prepared with consistently high levels of diastereo- and enantiocontrol. Moreover, this method constitutes the first report of an enantioselective desymmetrization of meso-cyclobutenes to prepare chiral cyclobutanes.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  asymmetric catalysis; boron; copper; cyclobutanes; cyclobutenes

Year:  2016        PMID： 27159674     DOI： 10.1002/anie.201601976

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


  21 in total

1.  Catalytic Enantioselective Synthesis of Cyclobutenes from Alkynes and Alkenyl Derivatives.

Authors:  Mahesh M Parsutkar; Vinayak Vishnu Pagar; T V RajanBabu
Journal:  J Am Chem Soc       Date:  2019-09-12       Impact factor: 15.419

2.  Accessing 1,2-Substituted Cyclobutanes through 1,2-Azaborine Photoisomerization.

Authors:  Zachary X Giustra; Xinyu Yang; Min Chen; Holger F Bettinger; Shih-Yuan Liu
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-07       Impact factor: 15.336

3.  Enantioselective C-H Arylation and Vinylation of Cyclobutyl Carboxylic Amides.

Authors:  Qing-Feng Wu; Xiao-Bing Wang; Peng-Xiang Shen; Jin-Quan Yu
Journal:  ACS Catal       Date:  2018-02-05       Impact factor: 13.084

4.  Ring-Opening Carbonyl-Olefin Metathesis of Cyclobutenes.

Authors:  Maxwell G Holl; Tristan H Lambert
Journal:  ACS Catal       Date:  2022-04-07       Impact factor: 13.700

5.  Stereocontrolled Pericyclic and Radical Cycloaddition Reactions of Readily Accessible Chiral Alkenyl Diazaborolidines.

Authors:  Mingkai Zhang; Peilin Xu; Alex J Vendola; Christophe Allais; Anne-Marie Dechert Schmitt; Robert A Singer; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2022-06-08       Impact factor: 16.823

6.  Photosensitized [2+2]-Cycloadditions of Alkenylboronates and Alkenes.

Authors:  Yanyao Liu; Dongshun Ni; Bernard G Stevenson; Vikrant Tripathy; Sarah E Braley; Krishnan Raghavachari; John R Swierk; M Kevin Brown
Journal:  Angew Chem Int Ed Engl       Date:  2022-04-21       Impact factor: 16.823

7.  PdII -Catalyzed Enantioselective C(sp3 )-H Arylation of Cyclobutyl Ketones Using a Chiral Transient Directing Group.

Authors:  Li-Jun Xiao; Kai Hong; Fan Luo; Liang Hu; William R Ewing; Kap-Sun Yeung; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2020-04-01       Impact factor: 15.336

8.  Chemical Synthesis and Self-Assembly of a Ladderane Phospholipid.

Authors:  Jaron A M Mercer; Carolyn M Cohen; Steven R Shuken; Anna M Wagner; Myles W Smith; Frank R Moss; Matthew D Smith; Riku Vahala; Alejandro Gonzalez-Martinez; Steven G Boxer; Noah Z Burns
Journal:  J Am Chem Soc       Date:  2016-11-29       Impact factor: 15.419

9.  Lessons in Strain and Stability: Enantioselective Synthesis of (+)-[5]-Ladderanoic Acid.

Authors:  Erin N Hancock; Erin L Kuker; Dean J Tantillo; M Kevin Brown
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-18       Impact factor: 15.336

10.  Construction of Complex Cyclobutane Building Blocks by Photosensitized [2 + 2] Cycloaddition of Vinyl Boronate Esters.

Authors:  Spencer O Scholz; Jesse B Kidd; Luca Capaldo; Niecia E Flikweert; Rowan M Littlefield; Tehshik P Yoon
Journal:  Org Lett       Date:  2021-04-12       Impact factor: 6.005
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