Literature DB >> 17308652

Organocatalytic asymmetric 5-hydroxyisoxazolidine synthesis: a highly enantioselective route to beta-amino acids.

Ismail Ibrahem1, Ramon Rios, Jan Vesely, Gui-Ling Zhao, Armando Córdova.   

Abstract

The highly chemo- and enantioselective organocatalytic tandem reaction between N-protected hydroxyl amines and alpha,beta-unsaturated aldehydes is presented; the reaction provides access to 5-hydroxyisoxazolidines and beta-amino acids in high yields and with 90-99% ee.

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Year:  2006        PMID： 17308652     DOI： 10.1039/b613410f

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  9 in total

1.  Asymmetric synthesis of enantiopure isoxazolidinone monomers for the synthesis of β-oligopeptides by chemoselective amide ligation.

Authors:  M Elisa Juarez-Garcia; Shouyun Yu; Jeffrey W Bode
Journal:  Tetrahedron       Date:  2010-06-26       Impact factor: 2.457

2.  Improved protocol for asymmetric, intramolecular heteroatom Michael addition using organocatalysis: enantioselective syntheses of homoproline, pelletierine, and homopipecolic acid.

Authors:  Erik C Carlson; Lauren K Rathbone; Hua Yang; Nathan D Collett; Rich G Carter
Journal:  J Org Chem       Date:  2008-06-05       Impact factor: 4.354

3.  Asymmetric aza-Michael reactions of alpha,beta-unsaturated ketones with bifunctional organic catalysts.

Authors:  Xiaojie Lu; Li Deng
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

4.  Enantioselective approach to quinolizidines: total synthesis of cermizine D and formal syntheses of senepodine G and cermizine C.

Authors:  Nagarathanam Veerasamy; Erik C Carlson; Nathan D Collett; Mrinmoy Saha; Rich G Carter
Journal:  J Org Chem       Date:  2013-04-29       Impact factor: 4.354

5.  An enantioselective Claisen rearrangement catalyzed by N-heterocyclic carbenes.

Authors:  Juthanat Kaeobamrung; Jessada Mahatthananchai; Pinguan Zheng; Jeffrey W Bode
Journal:  J Am Chem Soc       Date:  2010-07-07       Impact factor: 15.419

6.  Direct amination of homoenolates catalyzed by N-heterocyclic carbenes.

Authors:  Audrey Chan; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2008-02-09       Impact factor: 15.419

7.  Methyl 5-hy-droxy-3-phenyl-1,2-oxazolidine-5-carboxyl-ate.

Authors:  Jia Ye; Ya-Nan Liu; Yu Cheng
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-04-25

8.  Organocatalytic cascade aza-Michael/hemiacetal reaction between disubstituted hydrazines and α,β-unsaturated aldehydes: Highly diastereo- and enantioselective synthesis of pyrazolidine derivatives.

Authors:  Zhi-Cong Geng; Jian Chen; Ning Li; Xiao-Fei Huang; Yong Zhang; Ya-Wen Zhang; Xing-Wang Wang
Journal:  Beilstein J Org Chem       Date:  2012-10-09       Impact factor: 2.883

9.  Practical Asymmetric Synthesis of Sitagliptin Phosphate Monohydrate.

Authors:  Haoling Gao; Jiangang Yu; Chengsheng Ge; Qun Jiang
Journal:  Molecules       Date:  2018-06-13       Impact factor: 4.411
  9 in total

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