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Isothiourea-mediated stereoselective C-acylation of silyl ketene acetals.
Org Lett. 2010 Jun 04; 12(11):2660-3.OL

Abstract

Isothiourea DHPB promotes the diastereoselective C-acylation of silyl ketene acetals with anhydrides or benzoyl fluoride, giving 3-acyl-3-aryl or 3-acyl-3-alkylfuranones in excellent yields and stereoselectivities (up to 99:1 dr).

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Publisher Full Text (DOI)

Authors+Show Affiliations

Woods PA
EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St. Andrews KY16 9ST, UK.
Morrill LC
No affiliation info available
Lebl T
No affiliation info available
Slawin AM
No affiliation info available
Bragg RA
No affiliation info available
Smith AD
No affiliation info available

MeSH

AcetalsAcylationAnhydridesCatalysisEthylenesFuransKetonesMolecular StructureSilanesStereoisomerismThiourea

Pub Type(s)

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

Language

eng

PubMed ID

20459078

Citation

Woods, Philip A., et al. "Isothiourea-mediated Stereoselective C-acylation of Silyl Ketene Acetals." Organic Letters, vol. 12, no. 11, 2010, pp. 2660-3.
Woods PA, Morrill LC, Lebl T, et al. Isothiourea-mediated stereoselective C-acylation of silyl ketene acetals. Org Lett. 2010;12(11):2660-3.
Woods, P. A., Morrill, L. C., Lebl, T., Slawin, A. M., Bragg, R. A., & Smith, A. D. (2010). Isothiourea-mediated stereoselective C-acylation of silyl ketene acetals. Organic Letters, 12(11), 2660-3. https://doi.org/10.1021/ol1008747
Woods PA, et al. Isothiourea-mediated Stereoselective C-acylation of Silyl Ketene Acetals. Org Lett. 2010 Jun 4;12(11):2660-3. PubMed PMID: 20459078.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Isothiourea-mediated stereoselective C-acylation of silyl ketene acetals. AU - Woods,Philip A, AU - Morrill,Louis C, AU - Lebl,Tomas, AU - Slawin,Alexandra M Z, AU - Bragg,Ryan A, AU - Smith,Andrew D, PY - 2010/5/13/entrez PY - 2010/5/13/pubmed PY - 2010/8/18/medline SP - 2660 EP - 3 JF - Organic letters JO - Org Lett VL - 12 IS - 11 N2 - Isothiourea DHPB promotes the diastereoselective C-acylation of silyl ketene acetals with anhydrides or benzoyl fluoride, giving 3-acyl-3-aryl or 3-acyl-3-alkylfuranones in excellent yields and stereoselectivities (up to 99:1 dr). SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/20459078/Isothiourea_mediated_stereoselective_C_acylation_of_silyl_ketene_acetals_ L2 - https://doi.org/10.1021/ol1008747 DB - PRIME DP - Unbound Medicine ER -