Literature DB >> 12656601

Tandem N-alkylation-C-allylation reaction of alpha-imino esters with organoaluminums and allyltributyltin.

Yasuki Niwa1, Makoto Shimizu.   

Abstract

On treatment of various alpha-imino esters with organoaluminum reagents and allyltributyltin in the presence of benzoyl peroxide, the tandem reaction proceeded to give the N-alkylation-C-allylation products in good yields. The tandem N-alkyation-C-cyanation also proceeded using silyl or aluminum cyanide to give the aminonitrile in good yield.

Entities:  

Year:  2003        PMID： 12656601     DOI： 10.1021/ja029639o

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


  9 in total

1.  P(NMe2)3-Mediated Umpolung Alkylation and Nonylidic Olefination of α-Keto Esters.

Authors:  Sunewang Rixin Wang; Alexander T Radosevich
Journal:  Org Lett       Date:  2015-07-15       Impact factor: 6.005

2.  Catalytic asymmetric addition of dialkylzinc reagents to alpha-aldiminoesters.

Authors:  Sandeep Basra; Michael W Fennie; Marisa C Kozlowski
Journal:  Org Lett       Date:  2006-06-22       Impact factor: 6.005

3.  A facile approach to 2-alkoxyindolin-3-one and its application to the synthesis of N-benzyl matemone.

Authors:  Makoto Shimizu; Hayao Imazato; Isao Mizota; Yusong Zhu
Journal:  RSC Adv       Date:  2019-06-03       Impact factor: 4.036

4.  Double nucleophilic addition to iminomalonate, leading to the synthesis of quaternary α-amino diesters and desymmetrization of the products.

Authors:  Makoto Shimizu; Miki Mushika; Isao Mizota; Yusong Zhu
Journal:  RSC Adv       Date:  2019-07-29       Impact factor: 4.036

5.  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

6.  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

7.  An umpolung reaction of α-iminothioesters possessing a cyclopropyl group.

Authors:  Makoto Shimizu; Takayoshi Morimoto; Yusuke Yanagi; Isao Mizota; Yusong Zhu
Journal:  RSC Adv       Date:  2020-03-10       Impact factor: 4.036

8.  Preparation and facile addition reactions of iminium salts derived from amino ketene silyl acetal and amino silyl enol ether.

Authors:  Makoto Shimizu; Shingo Hata; Koichi Kondo; Kazuhiro Murakami; Isao Mizota; Yusong Zhu
Journal:  RSC Adv       Date:  2020-07-24       Impact factor: 4.036

9.  Asymmetric synthesis of α-allyl-α-aryl α-amino acids by tandem alkylation/π-allylation of α-iminoesters.

Authors:  John M Curto; Joshua S Dickstein; Simon Berritt; Marisa C Kozlowski
Journal:  Org Lett       Date:  2014-03-25       Impact factor: 6.005
  9 in total

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