Literature DB >> 17997567

Diphenylprolinol silyl ether as catalyst of an asymmetric, catalytic, and direct Michael reaction of nitroalkanes with alpha,beta-unsaturated aldehydes.

Hiroaki Gotoh1, Hayato Ishikawa, Yujiro Hayashi.   

Abstract

A catalytic enantioselective direct conjugate addition of nitroalkanes to alpha,beta-unsaturated aldehydes using diphenylprolinol silyl ether as an organocatalyst has been developed. Using this methodology as a key step, short syntheses of therapeutically useful compounds have also been accomplished.

Entities:  

Year:  2007        PMID: 17997567     DOI: 10.1021/ol702545z

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


  17 in total

1.  Three-component coupling reactions of silyl glyoxylates, vinyl Grignard reagent, and nitroalkenes: an efficient, highly diastereoselective approach to nitrocyclopentanols.

Authors:  Gregory R Boyce; Jeffrey S Johnson
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-15       Impact factor: 15.336

Review 2.  Asymmetric Michael Addition in Synthesis of β-Substituted GABA Derivatives.

Authors:  Jianlin Han; Jorge Escorihuela; Santos Fustero; Aitor Landa; Vadim A Soloshonok; Alexander Sorochinsky
Journal:  Molecules       Date:  2022-06-13       Impact factor: 4.927

3.  New preorganized γ-amino acids as foldamer building blocks.

Authors:  Li Guo; Weicheng Zhang; Ilia A Guzei; Lara C Spencer; Samuel H Gellman
Journal:  Org Lett       Date:  2012-05-08       Impact factor: 6.005

4.  Evaluation of a cyclopentane-based γ-amino acid for the ability to promote α/γ-peptide secondary structure.

Authors:  Michael W Giuliano; Stacy J Maynard; Aaron M Almeida; Andrew G Reidenbach; Li Guo; Emily C Ulrich; Ilia A Guzei; Samuel H Gellman
Journal:  J Org Chem       Date:  2013-12-05       Impact factor: 4.354

5.  An Asymmetric Vinylogous Michael Cascade of Silyl Glyoximide, Vinyl Grignard, and Nitroalkenes via Long Range Stereoinduction.

Authors:  Gregory R Boyce; Jeffrey S Johnson
Journal:  J Org Chem       Date:  2016-02-02       Impact factor: 4.354

6.  Pot economy and one-pot synthesis.

Authors:  Yujiro Hayashi
Journal:  Chem Sci       Date:  2016-01-06       Impact factor: 9.825

7.  Asymmetric Redox-Annulation of Cyclic Amines.

Authors:  YoungKu Kang; Weijie Chen; Martin Breugst; Daniel Seidel
Journal:  J Org Chem       Date:  2015-10-02       Impact factor: 4.354

Review 8.  Asymmetric organocatalysis at the service of medicinal chemistry.

Authors:  Alfredo Ricci
Journal:  ISRN Org Chem       Date:  2014-03-11

9.  Using mutability landscapes of a promiscuous tautomerase to guide the engineering of enantioselective Michaelases.

Authors:  Jan-Ytzen van der Meer; Harshwardhan Poddar; Bert-Jan Baas; Yufeng Miao; Mehran Rahimi; Andreas Kunzendorf; Ronald van Merkerk; Pieter G Tepper; Edzard M Geertsema; Andy-Mark W H Thunnissen; Wim J Quax; Gerrit J Poelarends
Journal:  Nat Commun       Date:  2016-03-08       Impact factor: 14.919

10.  Decarboxylative Annulation of α-Amino Acids with γ-Nitroaldehydes.

Authors:  YoungKu Kang; Daniel Seidel
Journal:  Org Lett       Date:  2016-08-10       Impact factor: 6.005

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