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Enantioselective nitro-Michael reactions catalyzed by short peptides on water.
Org Biomol Chem. 2009 Oct 21; 7(20):4279-84.OB

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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Publisher Full Text (DOI)

Authors+Show Affiliations

Freund M
Department of Chemistry and Pharmacy, Institute of Organic Chemistry 1, University of Erlangen-Nuremberg, Henkestrasse 42, 91054, Erlangen, Germany.
Schenker S
No affiliation info available
Tsogoeva SB
No affiliation info available

MeSH

CatalysisKetonesOligopeptidesProlineStereoisomerismStyreneSubstrate SpecificityWater

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

19795068

Citation

Freund, Matthias, et al. "Enantioselective nitro-Michael Reactions Catalyzed By Short Peptides On Water." Organic & Biomolecular Chemistry, vol. 7, no. 20, 2009, pp. 4279-84.
Freund M, Schenker S, Tsogoeva SB. Enantioselective nitro-Michael reactions catalyzed by short peptides on water. Org Biomol Chem. 2009;7(20):4279-84.
Freund, M., Schenker, S., & Tsogoeva, S. B. (2009). Enantioselective nitro-Michael reactions catalyzed by short peptides on water. Organic & Biomolecular Chemistry, 7(20), 4279-84. https://doi.org/10.1039/b910249c
Freund M, Schenker S, Tsogoeva SB. Enantioselective nitro-Michael Reactions Catalyzed By Short Peptides On Water. Org Biomol Chem. 2009 Oct 21;7(20):4279-84. PubMed PMID: 19795068.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective nitro-Michael reactions catalyzed by short peptides on water. AU - Freund,Matthias, AU - Schenker,Sebastian, AU - Tsogoeva,Svetlana B, Y1 - 2009/08/14/ PY - 2009/10/2/entrez PY - 2009/10/2/pubmed PY - 2010/1/6/medline SP - 4279 EP - 84 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 7 IS - 20 N2 - 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. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/19795068/Enantioselective_nitro_Michael_reactions_catalyzed_by_short_peptides_on_water_ L2 - https://doi.org/10.1039/b910249c DB - PRIME DP - Unbound Medicine ER -