95061-57-7

Upstream product

• 2043-61-0 cyclohexanecarbaldehyde 
• 17715-00-3 prop-2-ynylcyclohexane 
• 132539-51-6 (3-cyclohexylprop-1-ynyl)trimethylsilane 
• 132841-63-5 (Z)-(1R,4R)-1-Cyclohexyl-4-(dimethyl-phenyl-silanyl)-pent-2-en-1-ol 
• 91118-20-6 (1,3-bis(trimethylsilyl))-3-cyclohexylprop-1-yne 
• 931-50-0 cyclohexylmagnesium bromide 
• 215546-04-6 Acetic acid (E)-1-cyclohexyl-4-trimethylsilanyl-pent-2-enyl ester 
• 215546-06-8 Acetic acid (E)-4-cyclohexyl-1-methyl-4-trimethylsilanyl-but-2-enyl ester 
• 917-64-6 methyl magnesium iodide 
• 95061-56-6 1-t-butylthio-4-cyclohexyl-(E,Z)-1,-3-butadiene 
• 95061-56-6 ((1Z,3E)-4-tert-Butylsulfanyl-buta-1,3-dienyl)-cyclohexane 
• 95061-37-3 ((1Z,3E)-4-Isopropylsulfanyl-buta-1,3-dienyl)-cyclohexane 
• 95061-36-2 ((1Z,3E)-4-Propylsulfanyl-buta-1,3-dienyl)-cyclohexane 
• 215546-37-5 (E)-5-Cyclohexyl-5-(dimethyl-phenyl-silanyl)-pent-3-en-2-ol 

Relevant academic research and scientific papers

The stereochemistry of the vinylogous Peterson elimination

Base-induced eliminations of the vinylogous β-hydroxysilanes 7, 9, 11 and 12 are stereospecifically syn, giving largely the trans,trans-diene 8 from 7 and 11, the cis,trans-diene 10 from 9, and the trans,cis-diene 13 from 12. When a cis double bond is produced, it is selectively placed adjacent to the carbon atom that originally carried the hydroxy group. E2′ Reactions with silyl as the electrofugal group and acetate as the nucleofugal group, initiated by fluoride ion, are not stereospecific, but can be highly stereoselective in favour of the trans,trans-diene 8 when the carbon substituent at the silicon-bearing end is a cyclohexyl group and the double bond is cis, and in favour of the trans,cis-diene 13 when the carbon substituent at the silicon-bearing end is a methyl group and the double bond is trans. Attempts to use the Peterson reactions to make o-quinodimethanes stereospecifically failed, with no evidence of 1,4-elimination from the alcohols 40 and 41. The corresponding E2′ reaction from the esters using fluoride ion on the acetates or formates 46 and 47 gave stereoselectively the E,E-quinodimethane 48.

The Stereochemistry of the Vinylogous Peterson Elimination

The base-catalysed eliminations of the vinylogous β-hydroxysilanes 7, 9, 11 and 12 are stereospecifically syn, giving largely the trans,trans-diene 8 from 7 and 11, the cis,trans-diene 10 from 9, and the trans,cis-diene 13 from 12; when a cis double bond

Stereoselective Synthesis of 1,4-Disubstituted 1,3-Diene from Aldehyde Using Organotitanium Reagent

Organotitanium reagent generated from 1-t-butylthio-3-trimethylsilyl-1-propene condenses with aldehydes to give 1-t-butylthio-(E,Z)-1,3-alkadienes in a single step via (E)-erythro-β-hydroxysilane in a highly regio- and stereoselective manner. 1,4-Dialkyl-1,3-diene is obtained from the diene sulfide by crosscoupling reaction with Grignard reagent in the presence of nickel catalyst.The utility of the method is illustrated by application to the synthesis of Spilanthol, a naturally occurring insecticide from Spilanthese olerancae in five steps.

An E-Selective 1,3-Diene Synthesis from Moderated Ylides and Aldehydes

The synthesis of E-1,3-dienes by the Wittig reaction of aldehydes and ylides is described.

STEREOSELECTIVE SYNTHESIS OF 1,4-DISUBSTITUTED 1,3-DIENE

New synthetic methods for the preparation of 1,3-dienes are described.