Literature DB >> 28603976

α-Imino Esters in Organic Synthesis: Recent Advances.

Bagher Eftekhari-Sis1, Maryam Zirak2.   

Abstract

α-Imino esters are useful precursors for the synthesis of a variety of types of natural and unnatural α-amino acid derivatives, with a wide range of biological activities. Due to the adjacent ester group, α-imino esters are more reactive relative to other types of imines and undergo different kinds of reactions, including organometallics addition, metal catalyzed vinylation and alkynylation, aza-Henry, aza-Morita-Baylis-Hillman, imino-ene, Mannich-type, and cycloaddition reactions, as well as hydrogenation and reduction. This review discusses the mechanism, scope, and applications of the reactions of α-imino esters and related compounds in organic synthesis, covering the literature from the last 12 years.

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Year:  2017        PMID: 28603976     DOI: 10.1021/acs.chemrev.7b00064

Source DB:  PubMed          Journal:  Chem Rev        ISSN: 0009-2665            Impact factor:   60.622


  8 in total

1.  A Broad Substrate Scope of Aza-Friedel-Crafts Alkylation for the Synthesis of Quaternary α-Amino Esters.

Authors:  Guangkuan Zhao; Shyam S Samanta; Jessica Michieletto; Stéphane P Roche
Journal:  Org Lett       Date:  2020-07-10       Impact factor: 6.005

2.  Synthesis of Structurally Diverse 3-, 4-, 5-, and 6-Membered Heterocycles from Diisopropyl Iminomalonates and Soft C-Nucleophiles.

Authors:  Padmanabha V Kattamuri; Urmibhusan Bhakta; Surached Siriwongsup; Doo-Hyun Kwon; Lawrence B Alemany; Muhammed Yousufuddin; Daniel H Ess; László Kürti
Journal:  J Org Chem       Date:  2019-05-14       Impact factor: 4.354

3.  Practical asymmetric amine nucleophilic approach for the modular construction of protected α-quaternary amino acids.

Authors:  Teng Liu; Shaofei Ni; Wusheng Guo
Journal:  Chem Sci       Date:  2022-06-05       Impact factor: 9.969

4.  Asymmetric Synthesis of Protected Unnatural α-Amino Acids via Enantioconvergent Nickel-Catalyzed Cross-Coupling.

Authors:  Ze-Peng Yang; Dylan J Freas; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2021-06-03       Impact factor: 16.383

5.  Ni-catalyzed asymmetric hydrogenation of N-aryl imino esters for the efficient synthesis of chiral α-aryl glycines.

Authors:  Dan Liu; Bowen Li; Jianzhong Chen; Ilya D Gridnev; Deyue Yan; Wanbin Zhang
Journal:  Nat Commun       Date:  2020-11-23       Impact factor: 14.919

6.  N-Alkylation/aldol reaction of α-aldimino thioesters: a facile three-component coupling reaction.

Authors:  Makoto Shimizu; Asako Higashino; Isao Mizota; Yusong Zhu
Journal:  RSC Adv       Date:  2021-04-07       Impact factor: 3.361

7.  Enantioselective synthesis of α-amino ketones through palladium-catalyzed asymmetric arylation of α-keto imines.

Authors:  Wei Wen; Zhao-Pin Ai; Chang-Lin Yang; Chao-Xing Li; Zhu-Lian Wu; Tian Cai; Qi-Xiang Guo
Journal:  Chem Sci       Date:  2022-03-07       Impact factor: 9.825

8.  An expeditious route to sterically encumbered nonproteinogenic α-amino acid precursors using allylboronic acids.

Authors:  Samrat Sahu; Ganesh Karan; Lisa Roy; Modhu Sudan Maji
Journal:  Chem Sci       Date:  2022-01-28       Impact factor: 9.825

  8 in total

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