Palladium complex-catalysed carbocyclization–distannylation, –disilylation and –silastannylation of bis-dienes using distannanes, disilanes and silylstannanes
- 1 January 1995
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 5,p. 599-608
- https://doi.org/10.1039/p19950000599
Abstract
Bis-dienes 4 react with distannanes 1, disilanes 2, and silylstannanes 3 in the presence of a catalytic amount of a palladium complex to afford carbocyclization–distannylation, –disilylation and –silastannylation products in high yields. Reaction of distannanes 1a, b with bis-dienes 4a, b as well as reaction of disilane 2b with bis-diene 4d proceeded regio- and stereo-selectively to afford a single product: trans-(E),(Z) isomers. Regio- and stereo-selective reaction was also realized with the disilane 2b and bis-diene 4e to provide only trans-(E),(E) isomer. In other cases, the reactions proceeded regioselectively, but the stereoselectivity was modest. The X-ray crystal structures of the cyclopropanes 10 and 11 have been determined.Keywords
This publication has 46 references indexed in Scilit:
- Catalytic palladium-mediated tetraene carbocyclizations: 1,2- and 1,4-stereochemical control in a polycyclization reactionThe Journal of Organic Chemistry, 1993
- Catalytic palladium-mediated tetraene carbocyclizations: the cycloisomerizations of acyclic tetraenes to cyclized trienesJournal of the American Chemical Society, 1992
- Catalytic transition-metal-mediated tetraene carbocyclizations: a new carbocyclization via hydrosilylation?Organometallics, 1990
- Palladium-catalyzed cycloisomerizations of enynes and related reactionsAccounts of Chemical Research, 1990
- Catalytic palladium-mediated tetraene carbocyclizationsThe Journal of Organic Chemistry, 1989
- Transition metal-mediated cycloaddition reactions of alkynes in organic synthesisChemical Reviews, 1988
- Nickel-catalyzed intramolecular [4 + 4]-cycloadditions: a new method for the synthesis of polycycles containing eight-membered ringsJournal of the American Chemical Society, 1986
- Convenient synthesis of alkyl (Z)- and (E)-2,3-bis(trimethylstannyl)alk-2-enoates and N,N-dimethyl (E)-2,3-bis(trimethylstannyl)alk-2-enamidesJournal of the Chemical Society, Chemical Communications, 1986
- Synthesis of (Z)-1,2-bis(trimethylstannyl)-1-alkenes by platinum-catalysed addition of hexamethyldistannane to 1-alkynesJournal of Organometallic Chemistry, 1983
- Fluorinated polysilanes. Palladium catalyzed 1,4-addition of fluorodisilanes to conjugated diene and enone systemsJournal of Organometallic Chemistry, 1978