Literature DB >> 19795068

Enantioselective nitro-Michael reactions catalyzed by short peptides on water.

Matthias Freund1, Sebastian Schenker, Svetlana B Tsogoeva.   

Abstract

Simple unmodified N-proline-based di- and tripeptides in combination with sodium hydroxide additive catalyze the asymmetric Michael reaction of ketones with nitroolefins to furnish the corresponding gamma-nitroketones with up to 99% yield, 99:1 dr and 70% ee at room temperature and on water without any organic cosolvent.

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Year:  2009        PMID： 19795068     DOI： 10.1039/b910249c

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  3 in total

Review 1.  Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms.

Authors:  Anthony J Metrano; Alex J Chinn; Christopher R Shugrue; Elizabeth A Stone; Byoungmoo Kim; Scott J Miller
Journal:  Chem Rev       Date:  2020-09-24       Impact factor: 60.622

2.  A New Organocatalytic Desymmetrization Reaction Enables the Enantioselective Total Synthesis of Madangamine E.

Authors:  Shinya Shiomi; Benjamin D A Shennan; Ken Yamazaki; Ángel L Fuentes de Arriba; Dhananjayan Vasu; Trevor A Hamlin; Darren J Dixon
Journal:  J Am Chem Soc       Date:  2022-01-17       Impact factor: 15.419

3.  Asymmetric [4 + 2] annulation of 5H-thiazol-4-ones with a chiral dipeptide-based Brønsted base catalyst.

Authors:  Bo Zhu; Shuai Qiu; Jiangtao Li; Michelle L Coote; Richmond Lee; Zhiyong Jiang
Journal:  Chem Sci       Date:  2016-06-09       Impact factor: 9.825
  3 in total

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