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Enantioselective acylation of silyl ketene acetals through fluoride anion-binding catalysis.
J Am Chem Soc. 2011 Sep 07; 133(35):13872-5.JA

Abstract

A highly enantioselective acylation of silyl ketene acetals with acyl fluorides has been developed to generate useful α,α-disubstituted butyrolactone products. This transformation is promoted by a new thiourea catalyst and 4-pyrrolidinopyridine and represents the first example of enantioselective thiourea anion-binding catalysis with fluoride.

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Authors+Show Affiliations

Birrell JA
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, United States.
Desrosiers JN
No affiliation info available
Jacobsen EN
No affiliation info available

MeSH

4-ButyrolactoneAcetalsAcylationAnionsCatalysisEthylenesFluoridesKetonesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

21800916

Citation

Birrell, James A., et al. "Enantioselective Acylation of Silyl Ketene Acetals Through Fluoride Anion-binding Catalysis." Journal of the American Chemical Society, vol. 133, no. 35, 2011, pp. 13872-5.
Birrell JA, Desrosiers JN, Jacobsen EN. Enantioselective acylation of silyl ketene acetals through fluoride anion-binding catalysis. J Am Chem Soc. 2011;133(35):13872-5.
Birrell, J. A., Desrosiers, J. N., & Jacobsen, E. N. (2011). Enantioselective acylation of silyl ketene acetals through fluoride anion-binding catalysis. Journal of the American Chemical Society, 133(35), 13872-5. https://doi.org/10.1021/ja205602j
Birrell JA, Desrosiers JN, Jacobsen EN. Enantioselective Acylation of Silyl Ketene Acetals Through Fluoride Anion-binding Catalysis. J Am Chem Soc. 2011 Sep 7;133(35):13872-5. PubMed PMID: 21800916.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective acylation of silyl ketene acetals through fluoride anion-binding catalysis. AU - Birrell,James A, AU - Desrosiers,Jean-Nicolas, AU - Jacobsen,Eric N, Y1 - 2011/08/10/ PY - 2011/8/2/entrez PY - 2011/8/2/pubmed PY - 2011/12/22/medline SP - 13872 EP - 5 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 133 IS - 35 N2 - A highly enantioselective acylation of silyl ketene acetals with acyl fluorides has been developed to generate useful α,α-disubstituted butyrolactone products. This transformation is promoted by a new thiourea catalyst and 4-pyrrolidinopyridine and represents the first example of enantioselective thiourea anion-binding catalysis with fluoride. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/21800916/Enantioselective_acylation_of_silyl_ketene_acetals_through_fluoride_anion_binding_catalysis_ L2 - https://doi.org/10.1021/ja205602j DB - PRIME DP - Unbound Medicine ER -