Literature DB >> 19653671

Enantioselective Michael reactions of beta, beta-disubstituted nitroalkenes: a new approach to beta(2,2)-amino acids with hetero-quaternary stereocenters.

Hai-Hua Lu1, Fu-Gen Zhang, Xiang-Gao Meng, Shu-Wen Duan, Wen-Jing Xiao.   

Abstract

An atom-economic organocatalytic asymmetric Michael reaction of alpha,beta,beta-trisubstituted olefins has been successfully developed. The reaction exhibits excellent enantioselectivities under low loading of catalysts, and the conjugate addition products are valuable for the synthesis of novel beta(2,2)-amino acids and beta-peptides.

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Year:  2009        PMID： 19653671     DOI： 10.1021/ol901572x

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


  8 in total

Review 1.  Recent advances in C-heteroatom bond forming by asymmetric Michael addition.

Authors:  Majid M Heravi; Parvin Hajiabbasi
Journal:  Mol Divers       Date:  2013-12-31       Impact factor: 2.943

2.  C(sp3)-Arylation by Conformationally Accelerated Intramolecular Nucleophilic Aromatic Substitution (SNAr).

Authors:  Steven M Wales; Rakesh K Saunthwal; Jonathan Clayden
Journal:  Acc Chem Res       Date:  2022-05-27       Impact factor: 24.466

3.  Cation control of diastereoselectivity in iridium-catalyzed allylic substitutions. Formation of enantioenriched tertiary alcohols and thioethers by allylation of 5H-oxazol-4-ones and 5H-thiazol-4-ones.

Authors:  Wenyong Chen; John F Hartwig
Journal:  J Am Chem Soc       Date:  2013-12-19       Impact factor: 15.419

4.  Quaternary β2,2-amino acid derivatives by asymmetric addition of isoxazolidin-5-ones to para-quinone methides.

Authors:  Andreas Eitzinger; Michael Winter; Johannes Schörgenhumer; Mario Waser
Journal:  Chem Commun (Camb)       Date:  2019-12-12       Impact factor: 6.222

5.  Asymmetric synthesis of tertiary thiols and thioethers.

Authors:  Jonathan Clayden; Paul Maclellan
Journal:  Beilstein J Org Chem       Date:  2011-05-10       Impact factor: 2.883

6.  Asymmetric Synthesis of Tertiary Alcohols and Thiols via Nonstabilized Tertiary α-Oxy- and α-Thio-Substituted Organolithium Species.

Authors:  Alexander P Pulis; Ana Varela; Cinzia Citti; Pradip Songara; Daniele Leonori; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-07       Impact factor: 15.336

7.  Organocatalytic sulfa-Michael/aldol cascade: constructing functionalized 2,5-dihydrothiophenes bearing a quaternary carbon stereocenter.

Authors:  Xiao-Yu Zhu; Mei-Heng Lv; Ya-Nan Zhao; Li-Yan Lan; Wen-Ze Li; Lin-Jiu Xiao
Journal:  RSC Adv       Date:  2018-10-03       Impact factor: 4.036

8.  Highly enantioselective sulfa-Michael addition reactions using N-heterocyclic carbene as a non-covalent organocatalyst.

Authors:  Jiean Chen; Sixuan Meng; Leming Wang; Hongmei Tang; Yong Huang
Journal:  Chem Sci       Date:  2015-04-23       Impact factor: 9.825
  8 in total

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