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Catalytic, enantioselective [4 + 2]-cycloadditions of ketene enolates and o-quinones: efficient entry to chiral, alpha-oxygenated carboxylic acid derivatives.
J Am Chem Soc. 2006 Feb 15; 128(6):1810-1.JA

Abstract

We report catalytic, enantioselective [4 + 2]-cycloadditions of o-quinones with ketene enolates (derived from readily available acid chlorides) using cinchona alkaloid derivatives as catalysts to produce products in high enantiomeric excess (ee) and good to excellent yields. The thermodynamic driving force for these reactions is due in part to the restoration of aromaticity to the products. The resulting chiral, bicycloadducts can be synthetically manipulated in a variety of useful ways, for example to provide a flexible synthesis of alpha-oxygenated carboxylic acid derivatives.

Authors+Show Affiliations

Bekele T
Department of Chemistry, New Chemistry Building, Johns Hopkins University, 3400 North Charles Street, Baltimore, MD 21218, USA.
Shah MH
No affiliation info available
Wolfer J
No affiliation info available
Abraham CJ
No affiliation info available
Weatherwax A
No affiliation info available
Lectka T
No affiliation info available

MeSH

Carboxylic AcidsCatalysisChloranilCyclizationEthylenesKetonesOxidation-ReductionQuinonesStereoisomerism

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

16464078

Citation

Bekele, Tefsit, et al. "Catalytic, Enantioselective [4 + 2]-cycloadditions of Ketene Enolates and O-quinones: Efficient Entry to Chiral, Alpha-oxygenated Carboxylic Acid Derivatives." Journal of the American Chemical Society, vol. 128, no. 6, 2006, pp. 1810-1.
Bekele T, Shah MH, Wolfer J, et al. Catalytic, enantioselective [4 + 2]-cycloadditions of ketene enolates and o-quinones: efficient entry to chiral, alpha-oxygenated carboxylic acid derivatives. J Am Chem Soc. 2006;128(6):1810-1.
Bekele, T., Shah, M. H., Wolfer, J., Abraham, C. J., Weatherwax, A., & Lectka, T. (2006). Catalytic, enantioselective [4 + 2]-cycloadditions of ketene enolates and o-quinones: efficient entry to chiral, alpha-oxygenated carboxylic acid derivatives. Journal of the American Chemical Society, 128(6), 1810-1.
Bekele T, et al. Catalytic, Enantioselective [4 + 2]-cycloadditions of Ketene Enolates and O-quinones: Efficient Entry to Chiral, Alpha-oxygenated Carboxylic Acid Derivatives. J Am Chem Soc. 2006 Feb 15;128(6):1810-1. PubMed PMID: 16464078.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Catalytic, enantioselective [4 + 2]-cycloadditions of ketene enolates and o-quinones: efficient entry to chiral, alpha-oxygenated carboxylic acid derivatives. AU - Bekele,Tefsit, AU - Shah,Meha H, AU - Wolfer,Jamison, AU - Abraham,Ciby J, AU - Weatherwax,Anthony, AU - Lectka,Thomas, PY - 2006/2/9/pubmed PY - 2006/4/20/medline PY - 2006/2/9/entrez SP - 1810 EP - 1 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 128 IS - 6 N2 - We report catalytic, enantioselective [4 + 2]-cycloadditions of o-quinones with ketene enolates (derived from readily available acid chlorides) using cinchona alkaloid derivatives as catalysts to produce products in high enantiomeric excess (ee) and good to excellent yields. The thermodynamic driving force for these reactions is due in part to the restoration of aromaticity to the products. The resulting chiral, bicycloadducts can be synthetically manipulated in a variety of useful ways, for example to provide a flexible synthesis of alpha-oxygenated carboxylic acid derivatives. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/16464078/Catalytic_enantioselective_[4_+_2]_cycloadditions_of_ketene_enolates_and_o_quinones:_efficient_entry_to_chiral_alpha_oxygenated_carboxylic_acid_derivatives_ DB - PRIME DP - Unbound Medicine ER -