Nickel-Catalyzed Tandem Coupling of α,β-Enones, Alkynes, and Alkynyltins for the Regio- and Stereoselective Synthesis of Conjugated Enynes
- 15 November 1996
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 61 (23) , 8248-8255
- https://doi.org/10.1021/jo961236h
Abstract
The nickel-catalyzed reaction of α,β-enones 2 with alkynes 1, alkynyltins 6, and Me3SiCl was carried out by the successive construction of two carbon−carbon bonds to give enol silyl ethers 5, which were then hydrolyzed to conjugated enynes 7, with high regio- and stereoselectivities (isomeric purities: 92−98%).Keywords
This publication has 21 references indexed in Scilit:
- Nickel-Catalyzed Tandem Coupling of Chlorotrimethylsilane, .alpha.,.beta.-Enones, Alkynes, and DimethylzincOrganometallics, 1995
- Regio- and Stereoselective Synthesis of 3,6-Dien-1-ynes by Nickel-Catalyzed Coupling Reaction of Allyl Chlorides, 1-Alkynes, and AlkynyltinsThe Journal of Organic Chemistry, 1994
- Chemists Clean Up Synthesis With One-Pot ReactionsScience, 1994
- Palladium‐Catalyzed ‘Metallo‐Ene’‐Type Cyclization/Vinylstannane Coupling of 1‐Acetoxy‐octa‐2,7‐dienes and 1‐Acetoxy‐oct‐2‐en‐7‐ynesHelvetica Chimica Acta, 1993
- Zipper-mode cascade carbometallation for construction of polycyclic structuresPublished by Walter de Gruyter GmbH ,1992
- A practical reversed-polarity alternative to organocuprate conjugate addition chemistry. Halocarbon coupling reactions of enal- and enone-derived allylnickel reagentsJournal of the American Chemical Society, 1991
- Stereoselective cyclization of (2-bromophenyl)- and (2-iodophenyl)alkynes catalyzed by palladium(O) complexesThe Journal of Organic Chemistry, 1990
- Tetrakis(triphenylphosphine)palladium(0)Published by Wiley ,1972
- Organo (dipyridyl) nickel complexes. II. Stabilities of olefin-nickel bonds in olefin-cooridinated dipyridylnickel and dialkyl (dipyridyl) nickel complexesJournal of the American Chemical Society, 1971
- Preparation and Thermal Rearrangement of Several Dicyclopentadiene DerivativesJournal of the American Chemical Society, 1957