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An experimental and theoretical study of the mechanism of stannylcupration of alpha,beta-acetylenic ketones and esters.
Chemistry
March 2006
Department of Chemistry, Technical University of Denmark, Building 201 Kemitorvet, 2800 Kgs. Lyngby, Denmark.
The title reaction has been investigated by experimental and computational (DFT) techniques, and subsequently compared to the corresponding carbocupration reaction, with particular emphasis on the stereoselectivity. For stannylcupration of an ynone substrate, only the anti-addition product is observed, whereas for the corresponding ynoate substrate, the stereoselectivity can be affected by the reaction conditions: in the presence of methanol as proton donor, the initial syn-addition product can be trapped, whereas a syn/anti mixture is obtained in a non-protic solvent. This is in sharp contrast to the carbocupration of the same ynone substrate with a cyanocuprate (RCu(CN)Li), which is highly selective for syn-addition.
View Article and Find Full Text PDFAllylstannanes and vinylstannanes from stannylcupration of C-C multiple bonds. Recent advances and applications in organic synthesis.
Chem Soc Rev
November 2005
Departamento de Química Orgánica, Facultad de Ciencias, c/Dr Mergelina s/n, 47011 Valladolid, Spain.
The stannylcupration of allenes and alkynes has emerged as a powerful tool for the synthesis of allyl- and vinylorganostannanes. The regio- and stereoselectivity of this reaction depends upon the nature of the cuprate, the temperature and the structure of the allene or alkyne. The versatility and synthetic scope of the tin-synthons thus obtained is very wide.
View Article and Find Full Text PDFStannylcupration of Acetylenes Followed by Reaction with Epoxides: A Novel Annulation Strategy for the Synthesis of Cyclobutenes.
J Org Chem
October 1998
Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Valladolid, Valladolid 47011, Spain.
Regiospecific and stereoselective synthesis of functionalized and differently metalated alkenes by silyl- or stannylcupration of metalated acetylenes.
J Org Chem
March 2001
Departamento de Química Orgánica, Universidad de Valladolid, 47011-Valladolid, Spain.
Differently metalated vinylcuprate intermediates resulting from silyl- or stannylcupration of silyl- and tin-containing acetylenes reacted with a range of electrophiles, including chlorosilanes and chlorostannanes, affording regio- and stereodefined differently metalated vic and gem silyl- and tin-trisubstituted alkenes. Some of these functionalized polymetalated olefins are interesting synthons in organic chemistry.
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