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Catalytic, asymmetric, "interrupted" Feist-Bénary reactions.
J Am Chem Soc. 2005 Oct 26; 127(42):14566-7.JA

Abstract

Pyrimidine derivatives of the cinchona alkaloids function as excellent asymmetric catalysts for the "Interrupted" Feist-Bénary Reaction. This reaction produces highly substituted hydroxydihydrofurans from simple starting materials under mild conditions. The asymmetric reaction gives high enantioselectivities with unsubstituted bromoketones, and high enantio- and diastereoselectivities with substituted substrates. Mechanistic experiments suggest that the hydrobromide salt of the alkaloid derivative is the active catalyst for the reaction.

Authors+Show Affiliations

Department of Chemistry, Wesleyan University, Middletown, Connecticut 06459-0180, USA. mcalter@wesleyan.eduNo affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

16231897

Citation

Calter, Michael A., et al. "Catalytic, Asymmetric, "interrupted" Feist-Bénary Reactions." Journal of the American Chemical Society, vol. 127, no. 42, 2005, pp. 14566-7.
Calter MA, Phillips RM, Flaschenriem C. Catalytic, asymmetric, "interrupted" Feist-Bénary reactions. J Am Chem Soc. 2005;127(42):14566-7.
Calter, M. A., Phillips, R. M., & Flaschenriem, C. (2005). Catalytic, asymmetric, "interrupted" Feist-Bénary reactions. Journal of the American Chemical Society, 127(42), 14566-7.
Calter MA, Phillips RM, Flaschenriem C. Catalytic, Asymmetric, "interrupted" Feist-Bénary Reactions. J Am Chem Soc. 2005 Oct 26;127(42):14566-7. PubMed PMID: 16231897.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Catalytic, asymmetric, "interrupted" Feist-Bénary reactions. AU - Calter,Michael A, AU - Phillips,Ryan M, AU - Flaschenriem,Christine, PY - 2005/10/20/pubmed PY - 2006/1/25/medline PY - 2005/10/20/entrez SP - 14566 EP - 7 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 127 IS - 42 N2 - Pyrimidine derivatives of the cinchona alkaloids function as excellent asymmetric catalysts for the "Interrupted" Feist-Bénary Reaction. This reaction produces highly substituted hydroxydihydrofurans from simple starting materials under mild conditions. The asymmetric reaction gives high enantioselectivities with unsubstituted bromoketones, and high enantio- and diastereoselectivities with substituted substrates. Mechanistic experiments suggest that the hydrobromide salt of the alkaloid derivative is the active catalyst for the reaction. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/16231897/Catalytic_asymmetric_"interrupted"_Feist_Bénary_reactions_ DB - PRIME DP - Unbound Medicine ER -