Literature DB >> 24079819

Enantioselective intermolecular [2+2] photocycloadditions of isoquinolone mediated by a chiral hydrogen-bonding template.

Susannah C Coote1, Thorsten Bach.   

Abstract

The first examples of enantioselective intermolecular [2+2] photocycloadditions of isoquinolone with alkenes are reported. Photoreactions were carried out at low temperature in the presence of a chiral hydrogen-bonding template, which effectively shields one face of the substrate through formation of a hydrogen-bonded supramolecular complex. Functionalized cyclobutane products were obtained in excellent yields (86-98%) and with outstanding regio-, diastereo-, and enantioselectivity (88-99% ee).

Entities:  

Year:  2013        PMID： 24079819     DOI： 10.1021/ja408167r

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  17 in total

1.  Escaping from Flatland: [2 + 2] Photocycloaddition; Conformationally Constrained sp3-rich Scaffolds for Lead Generation.

Authors:  Brian Cox; Kevin I Booker-Milburn; Luke D Elliott; Michael Robertson-Ralph; Victor Zdorichenko
Journal:  ACS Med Chem Lett       Date:  2019-10-22       Impact factor: 4.345

2.  Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions.

Authors:  Saner Poplata; Andreas Tröster; You-Quan Zou; Thorsten Bach
Journal:  Chem Rev       Date:  2016-03-28       Impact factor: 60.622

3.  Expeditious Synthesis of Isoquinolones and Isocoumarins with a Vinyl Borane as an Acetylene Equivalent.

Authors:  Momar Toure; Saul Jaime-Figueroa; George M Burslem; Craig M Crews
Journal:  European J Org Chem       Date:  2016-07-26

4.  Diastereo- and Enantioselective CuH-Catalyzed Hydroamination of Strained Trisubstituted Alkenes.

Authors:  Sheng Feng; Hua Hao; Peng Liu; Stephen L Buchwald
Journal:  ACS Catal       Date:  2019-11-21       Impact factor: 13.084

Review 5.  Synthesis of cyclodextrin derivatives for enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate.

Authors:  Xueqin Wei; Jiecheng Ji; Yongxin Nie; Liangjian Tang; Ming Rao; Xiaoqian Wang; Wanhua Wu; Dan Su; Zhihui Zhong; Cheng Yang
Journal:  Nat Protoc       Date:  2022-08-31       Impact factor: 17.021

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.  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

Review 8.  Chiral Photocatalyst Structures in Asymmetric Photochemical Synthesis.

Authors:  Matthew J Genzink; Jesse B Kidd; Wesley B Swords; Tehshik P Yoon
Journal:  Chem Rev       Date:  2021-10-04       Impact factor: 60.622

9.  A Chiral Thiourea as a Template for Enantioselective Intramolecular [2 + 2] Photocycloaddition Reactions.

Authors:  Florian Mayr; Richard Brimioulle; Thorsten Bach
Journal:  J Org Chem       Date:  2016-06-09       Impact factor: 4.354

10.  Enantioselective Intermolecular [2 + 2] Photocycloaddition Reactions of 2(1H)-Quinolones Induced by Visible Light Irradiation.

Authors:  Andreas Tröster; Rafael Alonso; Andreas Bauer; Thorsten Bach
Journal:  J Am Chem Soc       Date:  2016-06-16       Impact factor: 15.419
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.