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Catalytic enantioselective synthesis of quaternary stereocenters via intermolecular C-acylation of silyl ketene acetals: dual activation of the electrophile and the nucleophile.
J Am Chem Soc. 2003 Apr 09; 125(14):4050-1.JA

Abstract

A nucleophile-catalyzed asymmetric intermolecular C-acylation of silyl ketene acetals by anhydrides has been developed, furnishing quaternary stereocenters with high enantioselectivity. Mechanistic studies support the hypothesis that the reaction involves activation both of the silyl ketene acetal (generation of an enolate) and of the anhydride (formation of an acylpyridinium ion).

Authors+Show Affiliations

Mermerian AH
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Fu GC
No affiliation info available

MeSH

AcetalsAcetic AnhydridesAcylationCatalysisEthylenesKetonesSilanesStereoisomerism

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

12670217

Citation

Mermerian, Ara H., and Gregory C. Fu. "Catalytic Enantioselective Synthesis of Quaternary Stereocenters Via Intermolecular C-acylation of Silyl Ketene Acetals: Dual Activation of the Electrophile and the Nucleophile." Journal of the American Chemical Society, vol. 125, no. 14, 2003, pp. 4050-1.
Mermerian AH, Fu GC. Catalytic enantioselective synthesis of quaternary stereocenters via intermolecular C-acylation of silyl ketene acetals: dual activation of the electrophile and the nucleophile. J Am Chem Soc. 2003;125(14):4050-1.
Mermerian, A. H., & Fu, G. C. (2003). Catalytic enantioselective synthesis of quaternary stereocenters via intermolecular C-acylation of silyl ketene acetals: dual activation of the electrophile and the nucleophile. Journal of the American Chemical Society, 125(14), 4050-1.
Mermerian AH, Fu GC. Catalytic Enantioselective Synthesis of Quaternary Stereocenters Via Intermolecular C-acylation of Silyl Ketene Acetals: Dual Activation of the Electrophile and the Nucleophile. J Am Chem Soc. 2003 Apr 9;125(14):4050-1. PubMed PMID: 12670217.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Catalytic enantioselective synthesis of quaternary stereocenters via intermolecular C-acylation of silyl ketene acetals: dual activation of the electrophile and the nucleophile. AU - Mermerian,Ara H, AU - Fu,Gregory C, PY - 2003/4/3/pubmed PY - 2003/5/20/medline PY - 2003/4/3/entrez SP - 4050 EP - 1 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 125 IS - 14 N2 - A nucleophile-catalyzed asymmetric intermolecular C-acylation of silyl ketene acetals by anhydrides has been developed, furnishing quaternary stereocenters with high enantioselectivity. Mechanistic studies support the hypothesis that the reaction involves activation both of the silyl ketene acetal (generation of an enolate) and of the anhydride (formation of an acylpyridinium ion). SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/12670217/Catalytic_enantioselective_synthesis_of_quaternary_stereocenters_via_intermolecular_C_acylation_of_silyl_ketene_acetals:_dual_activation_of_the_electrophile_and_the_nucleophile_ DB - PRIME DP - Unbound Medicine ER -