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Regio- and stereoselective enyne cross metathesis of silylated internal alkynes.
J Am Chem Soc. 2004 Aug 25; 126(33):10242-3.JA

Abstract

Cross metathesis between silylalkynes and various functionalized alkenes catalyzed by Grubbs carbene complex produced, in most cases, single regio- and stereoisomers of the resultant 1,3-dienes. Polar heteroatom substituents at the propargylic site are important for high reactivity and selectivity. An important mechanistic insight regarding the initiation event and the key propagating alkylidene in this reaction was obtained by employing a tandem cross metathesis ring-closing metathesis between a terminal alkene and a silylated alkyne possessing an alkene tether.

Authors+Show Affiliations

Kim M
Department of Chemistry, University of Wisconsin, Madison, WI 53706, USA.
Park S
No affiliation info available
Maifeld SV
No affiliation info available
Lee D
No affiliation info available

MeSH

AlkenesAlkynesOrganosilicon CompoundsStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

15315426

Citation

Kim, Mansuk, et al. "Regio- and Stereoselective Enyne Cross Metathesis of Silylated Internal Alkynes." Journal of the American Chemical Society, vol. 126, no. 33, 2004, pp. 10242-3.
Kim M, Park S, Maifeld SV, et al. Regio- and stereoselective enyne cross metathesis of silylated internal alkynes. J Am Chem Soc. 2004;126(33):10242-3.
Kim, M., Park, S., Maifeld, S. V., & Lee, D. (2004). Regio- and stereoselective enyne cross metathesis of silylated internal alkynes. Journal of the American Chemical Society, 126(33), 10242-3.
Kim M, et al. Regio- and Stereoselective Enyne Cross Metathesis of Silylated Internal Alkynes. J Am Chem Soc. 2004 Aug 25;126(33):10242-3. PubMed PMID: 15315426.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Regio- and stereoselective enyne cross metathesis of silylated internal alkynes. AU - Kim,Mansuk, AU - Park,Sangho, AU - Maifeld,Sarah V, AU - Lee,Daesung, PY - 2004/8/19/pubmed PY - 2004/11/13/medline PY - 2004/8/19/entrez SP - 10242 EP - 3 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 126 IS - 33 N2 - Cross metathesis between silylalkynes and various functionalized alkenes catalyzed by Grubbs carbene complex produced, in most cases, single regio- and stereoisomers of the resultant 1,3-dienes. Polar heteroatom substituents at the propargylic site are important for high reactivity and selectivity. An important mechanistic insight regarding the initiation event and the key propagating alkylidene in this reaction was obtained by employing a tandem cross metathesis ring-closing metathesis between a terminal alkene and a silylated alkyne possessing an alkene tether. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/15315426/Regio__and_stereoselective_enyne_cross_metathesis_of_silylated_internal_alkynes_ DB - PRIME DP - Unbound Medicine ER -