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Isothiourea-catalysed asymmetric C-acylation of silyl ketene acetals.
Chemistry. 2011 Sep 19; 17(39):11060-7.C

Abstract

Screening of a range of chiral isothioureas and acyl donors to promote the asymmetric C-acylation of silyl ketene acetals indicates that C(2)-aryl-dihydropyrimidobenzothiazole-derived isothioureas and propionic anhydride give optimal reactivity and enantioselectivity in this process. Under optimised conditions 3-acyl-3-aryl or 3-acyl-3-alkylfuranones are prepared in good yields and moderate to excellent enantioselectivities (up to 98% ee; ee=enantiomeric excess).

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Publisher Full Text (DOI)

Authors+Show Affiliations

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

MeSH

AcetalsAcylationCatalysisEthylenesFuransKetonesSilanesStereoisomerismThiourea

Pub Type(s)

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

Language

eng

PubMed ID

21853484

Citation

Woods, Philip A., et al. "Isothiourea-catalysed Asymmetric C-acylation of Silyl Ketene Acetals." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 17, no. 39, 2011, pp. 11060-7.
Woods PA, Morrill LC, Bragg RA, et al. Isothiourea-catalysed asymmetric C-acylation of silyl ketene acetals. Chemistry. 2011;17(39):11060-7.
Woods, P. A., Morrill, L. C., Bragg, R. A., & Smith, A. D. (2011). Isothiourea-catalysed asymmetric C-acylation of silyl ketene acetals. Chemistry (Weinheim an Der Bergstrasse, Germany), 17(39), 11060-7. https://doi.org/10.1002/chem.201100995
Woods PA, et al. Isothiourea-catalysed Asymmetric C-acylation of Silyl Ketene Acetals. Chemistry. 2011 Sep 19;17(39):11060-7. PubMed PMID: 21853484.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Isothiourea-catalysed asymmetric C-acylation of silyl ketene acetals. AU - Woods,Philip A, AU - Morrill,Louis C, AU - Bragg,Ryan A, AU - Smith,Andrew D, Y1 - 2011/08/18/ PY - 2011/04/01/received PY - 2011/05/31/revised PY - 2011/8/20/entrez PY - 2011/8/20/pubmed PY - 2012/1/10/medline SP - 11060 EP - 7 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 17 IS - 39 N2 - Screening of a range of chiral isothioureas and acyl donors to promote the asymmetric C-acylation of silyl ketene acetals indicates that C(2)-aryl-dihydropyrimidobenzothiazole-derived isothioureas and propionic anhydride give optimal reactivity and enantioselectivity in this process. Under optimised conditions 3-acyl-3-aryl or 3-acyl-3-alkylfuranones are prepared in good yields and moderate to excellent enantioselectivities (up to 98% ee; ee=enantiomeric excess). SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/21853484/Isothiourea_catalysed_asymmetric_C_acylation_of_silyl_ketene_acetals_ L2 - https://doi.org/10.1002/chem.201100995 DB - PRIME DP - Unbound Medicine ER -