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Enantioselective nitroaldol reaction of alpha-ketoesters catalyzed by cinchona alkaloids.
J Am Chem Soc. 2006 Jan 25; 128(3):732-3.JA

Abstract

The development of highly enantioselective and general catalytic nitroaldol (Henry) reactions with ketones is a challenging yet desirable task in organic synthesis. In this communication, we report an asymmetric nitroaldol reaction with alpha-ketoesters catalyzed by a new C6'-OH cinchona alkaloid catalyst. This is the first highly efficient organocatalytic asymmetric Henry reaction with ketones. This reaction is operationally simple and affords high enantioselectivity as well as good to excellent yield for a broad range of alpha-ketoesters.

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Authors+Show Affiliations

Li H
Department of Chemistry, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
Wang B
No affiliation info available
Deng L
No affiliation info available

MeSH

AldehydesCatalysisCinchona AlkaloidsEstersKetonesNitro CompoundsStereoisomerism

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural

Language

eng

PubMed ID

16417358

Citation

Li, Hongming, et al. "Enantioselective Nitroaldol Reaction of Alpha-ketoesters Catalyzed By Cinchona Alkaloids." Journal of the American Chemical Society, vol. 128, no. 3, 2006, pp. 732-3.
Li H, Wang B, Deng L. Enantioselective nitroaldol reaction of alpha-ketoesters catalyzed by cinchona alkaloids. J Am Chem Soc. 2006;128(3):732-3.
Li, H., Wang, B., & Deng, L. (2006). Enantioselective nitroaldol reaction of alpha-ketoesters catalyzed by cinchona alkaloids. Journal of the American Chemical Society, 128(3), 732-3.
Li H, Wang B, Deng L. Enantioselective Nitroaldol Reaction of Alpha-ketoesters Catalyzed By Cinchona Alkaloids. J Am Chem Soc. 2006 Jan 25;128(3):732-3. PubMed PMID: 16417358.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective nitroaldol reaction of alpha-ketoesters catalyzed by cinchona alkaloids. AU - Li,Hongming, AU - Wang,Baomin, AU - Deng,Li, PY - 2006/1/19/pubmed PY - 2006/4/7/medline PY - 2006/1/19/entrez SP - 732 EP - 3 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 128 IS - 3 N2 - The development of highly enantioselective and general catalytic nitroaldol (Henry) reactions with ketones is a challenging yet desirable task in organic synthesis. In this communication, we report an asymmetric nitroaldol reaction with alpha-ketoesters catalyzed by a new C6'-OH cinchona alkaloid catalyst. This is the first highly efficient organocatalytic asymmetric Henry reaction with ketones. This reaction is operationally simple and affords high enantioselectivity as well as good to excellent yield for a broad range of alpha-ketoesters. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/16417358/Enantioselective_nitroaldol_reaction_of_alpha_ketoesters_catalyzed_by_cinchona_alkaloids_ DB - PRIME DP - Unbound Medicine ER -