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Cinchona alkaloid-lewis acid catalyst systems for enantioselective ketene-aldehyde cycloadditions.
J Am Chem Soc. 2004 May 05; 126(17):5352-3.JA

Abstract

Asymmetric cinchona alkaloid-catalyzed acid chloride-aldehyde cyclocondensation (AAC) reactions afford enantioenriched 4-substituted and 3,4-disubstituted beta-lactones with near perfect absolute and relative stereocontrol. These reactions are characterized by the operational simplicity derived from using commercially available or easily obtained (one-step) reaction catalysts and in situ ketene generation from acid chlorides. The range of aldehyde substrates that serve as effective AAC substrates include sterically hindered aldehydes such as cyclohexanecarboxaldehyde and pivaldehyde.

Authors+Show Affiliations

Zhu C
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.
Shen X
No affiliation info available
Nelson SG
No affiliation info available

MeSH

AcidsAldehydesCatalysisCinchona AlkaloidsEthylenesHydrogen-Ion ConcentrationKetonesMagnetic Resonance SpectroscopyMolecular StructureStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

15113194

Citation

Zhu, Cheng, et al. "Cinchona Alkaloid-lewis Acid Catalyst Systems for Enantioselective Ketene-aldehyde Cycloadditions." Journal of the American Chemical Society, vol. 126, no. 17, 2004, pp. 5352-3.
Zhu C, Shen X, Nelson SG. Cinchona alkaloid-lewis acid catalyst systems for enantioselective ketene-aldehyde cycloadditions. J Am Chem Soc. 2004;126(17):5352-3.
Zhu, C., Shen, X., & Nelson, S. G. (2004). Cinchona alkaloid-lewis acid catalyst systems for enantioselective ketene-aldehyde cycloadditions. Journal of the American Chemical Society, 126(17), 5352-3.
Zhu C, Shen X, Nelson SG. Cinchona Alkaloid-lewis Acid Catalyst Systems for Enantioselective Ketene-aldehyde Cycloadditions. J Am Chem Soc. 2004 May 5;126(17):5352-3. PubMed PMID: 15113194.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Cinchona alkaloid-lewis acid catalyst systems for enantioselective ketene-aldehyde cycloadditions. AU - Zhu,Cheng, AU - Shen,Xiaoqiang, AU - Nelson,Scott G, PY - 2004/4/29/pubmed PY - 2004/8/18/medline PY - 2004/4/29/entrez SP - 5352 EP - 3 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 126 IS - 17 N2 - Asymmetric cinchona alkaloid-catalyzed acid chloride-aldehyde cyclocondensation (AAC) reactions afford enantioenriched 4-substituted and 3,4-disubstituted beta-lactones with near perfect absolute and relative stereocontrol. These reactions are characterized by the operational simplicity derived from using commercially available or easily obtained (one-step) reaction catalysts and in situ ketene generation from acid chlorides. The range of aldehyde substrates that serve as effective AAC substrates include sterically hindered aldehydes such as cyclohexanecarboxaldehyde and pivaldehyde. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/15113194/Cinchona_alkaloid_lewis_acid_catalyst_systems_for_enantioselective_ketene_aldehyde_cycloadditions_ DB - PRIME DP - Unbound Medicine ER -