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• W2137029176 endingPage "4004" @default.
• W2137029176 startingPage "3989" @default.
• W2137029176 abstract "R-5-Methylcyclohex-2-enone 1 reacts successively with the phenyldimethylsilylzincate reagent and acetaldehyde to give with regiocontrol the aldols 7, dehydration of which creates the E-exocyclic double bond of the alpha,beta-unsaturated ketone 2. Conjugate addition of the ethylcuprate reagent to this compound takes place with high (96:4) selectivity in favour of the R stereoisomer 12, hydrolysis of which gives (2R,3R,5S,2'R)-2-(but-2'-yl)-3-dimethyl(phenyl)silyl-5-methylcyclohexanone 3. The oxime acetate of this ketone undergoes fragmentation in the presence of trimethylsilyl trifluoromethanesulfonate to give 3R,7R,5E-3,7-dimethylnon-5-enonitrile 4, in which an open-chain 1,5-stereochemical relationship is set up with a high level of stereocontrol. A similar sequence adding 4-methylpentylcuprate to the enone 2, and fragmentation gives 3R,7R,5E-3,7,11-trimethyldodec-5-enonitrile 20. Reduction and hydrogenation of this nitrile gives 3R,7R-3,7,11-trimethyldodecanal 22, which can be converted into phytol 25. The ketoaldehyde 29 reacts with samarium iodide to give only the alcohol 30, in which the radical anion has attacked from the top surface just like the cuprate reagents in their reactions with the ketone 2." @default.
• W2137029176 created "2016-06-24" @default.
• W2137029176 creator A5016076162 @default.
• W2137029176 creator A5032069177 @default.
• W2137029176 creator A5072268460 @default.
• W2137029176 date "2003-01-01" @default.
• W2137029176 modified "2023-10-05" @default.
• W2137029176 title "Stereocontrol of 1,5-related stereocentres using an intermediate silyl group—the diastereoselectivity of nucleophilic attack on a double bond adjacent to a stereogenic centre carrying a silyl group" @default.
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• W2137029176 doi "https://doi.org/10.1039/b305880h" @default.
• W2137029176 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/14664388" @default.
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