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Catalytic, asymmetric preparation of ketene dimers from acid chlorides.
Org Lett. 2003 Nov 27; 5(24):4745-8.OL

Abstract

[reaction: see text] The cinchona alkaloid-catalyzed dimerization of monosubstituted ketenes generated in situ from the reaction of acid chlorides and diisopropylethylamine yields ketene dimers in high yields and enantioselectivities. This reaction tolerates sterically demanding and functionally diverse substituents. Kinetic studies suggest that the rate-determining step for the reaction is the deprotonation of the acid chloride by the tertiary amine to form ketene and that the stereochemistry-forming step is addition of an ammonium enolate with ketene.

Authors+Show Affiliations

Calter MA
Department of Chemistry, University of Rochester, Rochester, New York 14627-0216, USA. calter@chem.rochester.edu
Orr RK
No affiliation info available
Song W
No affiliation info available

MeSH

AcidsCatalysisChloridesDimerizationEthylenesKetonesMagnetic Resonance SpectroscopyMolecular StructureStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

14627430

Citation

Calter, Michael A., et al. "Catalytic, Asymmetric Preparation of Ketene Dimers From Acid Chlorides." Organic Letters, vol. 5, no. 24, 2003, pp. 4745-8.
Calter MA, Orr RK, Song W. Catalytic, asymmetric preparation of ketene dimers from acid chlorides. Org Lett. 2003;5(24):4745-8.
Calter, M. A., Orr, R. K., & Song, W. (2003). Catalytic, asymmetric preparation of ketene dimers from acid chlorides. Organic Letters, 5(24), 4745-8.
Calter MA, Orr RK, Song W. Catalytic, Asymmetric Preparation of Ketene Dimers From Acid Chlorides. Org Lett. 2003 Nov 27;5(24):4745-8. PubMed PMID: 14627430.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Catalytic, asymmetric preparation of ketene dimers from acid chlorides. AU - Calter,Michael A, AU - Orr,Robert K, AU - Song,Wei, PY - 2003/11/25/pubmed PY - 2003/12/3/medline PY - 2003/11/25/entrez SP - 4745 EP - 8 JF - Organic letters JO - Org Lett VL - 5 IS - 24 N2 - [reaction: see text] The cinchona alkaloid-catalyzed dimerization of monosubstituted ketenes generated in situ from the reaction of acid chlorides and diisopropylethylamine yields ketene dimers in high yields and enantioselectivities. This reaction tolerates sterically demanding and functionally diverse substituents. Kinetic studies suggest that the rate-determining step for the reaction is the deprotonation of the acid chloride by the tertiary amine to form ketene and that the stereochemistry-forming step is addition of an ammonium enolate with ketene. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/14627430/Catalytic_asymmetric_preparation_of_ketene_dimers_from_acid_chlorides_ DB - PRIME DP - Unbound Medicine ER -