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Stereoselective synthesis of vinylsilanes by a gold(I)-catalyzed acetylenic sila-cope rearrangement.
J Am Chem Soc. 2006 Sep 06; 128(35):11364-5.JA

Abstract

Cationic tri-tert-butylphosphinegold(I) serves as a catalyst in the sila-Cope rearrangement of acetylenic allylsilanes. When phenol is employed as a nucleophile, the reaction allows for the stereoselective synthesis of vinylsilanes. Alternatively, use of methanol as a nucleophile leads to cyclic vinylsilanes, which can be viewed as latent vinylsilanes that are revealed on treatment with a mild Lewis acid. Thus, both of these reagents serve as useful reagents for stereoselective synthesis of trisubstituted olefins through transition-metal-catalyzed cross-coupling reactions.

Authors+Show Affiliations

Horino Y
Department of Chemistry, University of California, Berkeley, California 94720, USA.
Luzung MR
No affiliation info available
Toste FD
No affiliation info available

MeSH

AlkynesAllyl CompoundsCatalysisCyclizationGoldMolecular StructurePhosphinesSilanesStereoisomerismVinyl Compounds

Pub Type(s)

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

Language

eng

PubMed ID

16939254

Citation

Horino, Yoshikazu, et al. "Stereoselective Synthesis of Vinylsilanes By a gold(I)-catalyzed Acetylenic Sila-cope Rearrangement." Journal of the American Chemical Society, vol. 128, no. 35, 2006, pp. 11364-5.
Horino Y, Luzung MR, Toste FD. Stereoselective synthesis of vinylsilanes by a gold(I)-catalyzed acetylenic sila-cope rearrangement. J Am Chem Soc. 2006;128(35):11364-5.
Horino, Y., Luzung, M. R., & Toste, F. D. (2006). Stereoselective synthesis of vinylsilanes by a gold(I)-catalyzed acetylenic sila-cope rearrangement. Journal of the American Chemical Society, 128(35), 11364-5.
Horino Y, Luzung MR, Toste FD. Stereoselective Synthesis of Vinylsilanes By a gold(I)-catalyzed Acetylenic Sila-cope Rearrangement. J Am Chem Soc. 2006 Sep 6;128(35):11364-5. PubMed PMID: 16939254.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Stereoselective synthesis of vinylsilanes by a gold(I)-catalyzed acetylenic sila-cope rearrangement. AU - Horino,Yoshikazu, AU - Luzung,Michael R, AU - Toste,F Dean, PY - 2006/8/31/pubmed PY - 2007/8/9/medline PY - 2006/8/31/entrez SP - 11364 EP - 5 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 128 IS - 35 N2 - Cationic tri-tert-butylphosphinegold(I) serves as a catalyst in the sila-Cope rearrangement of acetylenic allylsilanes. When phenol is employed as a nucleophile, the reaction allows for the stereoselective synthesis of vinylsilanes. Alternatively, use of methanol as a nucleophile leads to cyclic vinylsilanes, which can be viewed as latent vinylsilanes that are revealed on treatment with a mild Lewis acid. Thus, both of these reagents serve as useful reagents for stereoselective synthesis of trisubstituted olefins through transition-metal-catalyzed cross-coupling reactions. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/16939254/Stereoselective_synthesis_of_vinylsilanes_by_a_gold_I__catalyzed_acetylenic_sila_cope_rearrangement_ L2 - https://doi.org/10.1021/ja0636800 DB - PRIME DP - Unbound Medicine ER -