Literature DB >> 12027636

Highly enhanced enantioselectivity in the memory of chirality via acyliminium ions.

G Ng'ang'a Wanyoike1, Osamu Onomura, Toshihide Maki, Yoshihiro Matsumura.   

Abstract

[reaction: see text] Electrochemical oxidation of N-acylated serine derivative 1b in methanol gave optically active methoxylated compound 2b with an enantiomeric excess of up to 80%. The bulky o-phenyl benzoyl N-protecting group was found to be the main contributing factor for the enhanced enantioselectivity. The mechanistic aspect of this methoxylation reaction was investigated and found to proceed via a retention mechanism.

Entities:  

Year:  2002        PMID： 12027636     DOI： 10.1021/ol025865r

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


  8 in total

1.  Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance.

Authors:  Ming Yan; Yu Kawamata; Phil S Baran
Journal:  Chem Rev       Date:  2017-10-09       Impact factor: 60.622

Review 2.  Enantioselective synthesis of heterocyclic compounds using photochemical reactions.

Authors:  Norbert Hoffmann
Journal:  Photochem Photobiol Sci       Date:  2021-11-25       Impact factor: 3.982

3.  Radical reactions with double memory of chirality (2MOC) for the enantiospecific synthesis of adjacent stereogenic quaternary centers in solution: cleavage and bonding faster than radical rotation.

Authors:  Marino J E Resendiz; Farnosh Family; Kerrian Fuller; Luis M Campos; Saeed I Khan; Natalia V Lebedeva; Malcolm D E Forbes; Miguel A Garcia-Garibay
Journal:  J Am Chem Soc       Date:  2009-06-24       Impact factor: 15.419

4.  Synthesis of N-Protected 1-Aminoalkylphosphonium Salts from Amides, Carbamates, Lactams, or Imides.

Authors:  Jakub Adamek; Paulina Zieleźny; Karol Erfurt
Journal:  J Org Chem       Date:  2021-04-08       Impact factor: 4.354

5.  Memory of chirality in a room temperature flow electrochemical reactor.

Authors:  Tomas Hardwick; Rossana Cicala; Thomas Wirth; Nisar Ahmed
Journal:  Sci Rep       Date:  2020-10-06       Impact factor: 4.996

6.  Non-Kolbe electrolysis of N-protected-α-amino acids: a standardized method for the synthesis of N-protected (1-methoxyalkyl)amines.

Authors:  A Walęcka-Kurczyk; J Adamek; K Walczak; M Michalak; A Październiok-Holewa
Journal:  RSC Adv       Date:  2022-01-12       Impact factor: 3.361

7.  Electrochemical oxidative decarboxylation and 1,2-aryl migration towards the synthesis of 1,2-diaryl ethers.

Authors:  Faxiang Bu; Lijun Lu; Xia Hu; Shengchun Wang; Heng Zhang; Aiwen Lei
Journal:  Chem Sci       Date:  2020-09-02       Impact factor: 9.825

8.  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
  8 in total

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