Literature DB >> 28045272

α-Arylation of α-Amino Acid Derivatives with Arynes via Memory of Chirality: Asymmetric Synthesis of Benzocyclobutenones with Tetrasubstituted Carbon.

Koji Kasamatsu1, Tomoyuki Yoshimura2, Attila Mandi3, Tohru Taniguchi3, Kenji Monde3, Takumi Furuta1, Takeo Kawabata1.   

Abstract

A method for asymmetric α-arylation of α-amino acid derivatives via memory of chirality has been developed. Addition of axially chiral enolates, generated from α-amino acid derivatives, to in situ generated arynes, followed by intramolecular C-acylation of the resulting aryl metallic species, gave benzocyclobutenones with a tetrasubstituted carbon with retention of configuration in up to 99% ee.

Entities:  

Year:  2017        PMID: 28045272     DOI: 10.1021/acs.orglett.6b03533

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


  3 in total

1.  Palladium-Catalyzed Access to Benzocyclobutenone-Derived Ketonitrones via C(sp2)-H Functionalization.

Authors:  Jakub Brześkiewicz; Rafał Loska
Journal:  Org Lett       Date:  2022-05-25       Impact factor: 6.072

2.  Tertiary amine-directed and involved carbonylative cyclizations through Pd/Cu-cocatalyzed multiple C-X (X = H or N) bond cleavage.

Authors:  Qiu-Chao Mu; Yi-Xue Nie; Xing-Feng Bai; Jing Chen; Lei Yang; Zheng Xu; Li Li; Chun-Gu Xia; Li-Wen Xu
Journal:  Chem Sci       Date:  2019-08-19       Impact factor: 9.825

3.  Memory of Chirality as a Prominent Pathway for the Synthesis of Natural Products through Chiral Intermediates.

Authors:  Tomas Hardwick; Nisar Ahmed
Journal:  ChemistryOpen       Date:  2018-06-19       Impact factor: 2.911

  3 in total

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