By Jaemoon Yang
Chapter 1 [3,3]?Sigmatropic Rearrangements (pages 5–48):
Chapter 2 Aldol Reactions (pages 49–96):
Chapter three steel Allylation Reactions (pages 97–145):
Chapter four Stereoselective discount rates (pages 147–195):
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Extra resources for Six-Membered Transition States in Organic Synthesis
Cope Ireland–Claisen 200°C OTIPS OTIPS OTIPS H O O O 5 4 1. KF, HMPA (30% from 4) 2. 4d A solution of the silylketene acetal 4 in dodecane was subjected to thermolysis ◦ at 200 C for 140 minutes. The Cope–Claisen rearrangement product 5 was then treated with KF in HMPA followed by esterification to afford the methyl ester 6. Fox et al. 4d). Lithiation of the optically active iodide 8 with t-BuLi followed by condensation of the resulting organolithium species with the amide 9 afforded the cyclopropyl ketone 10.
Nowlan, D. , III; Gregg, T. ; Davies, H. M. ; Singleton, D. A. J. Am. Chem. Soc. 2003, 125 , 15902. 5. 5a). 5b). The oxy-Cope rearrangement would be a synthetically useful route to access δ,ε-unsaturated carbonyl compounds from the corresponding secondary or tertiary alcohols if the reaction conditions were mild. In 1975, Evans and Golob discovered that the Cope rearrangement of 3-hydroxy-1,5-hexadienes proceeds extremely fast in the presence ◦of potassium hydride. 5c). 1 equivalents of 18-crown-6.
4d). Lithiation of the optically active iodide 8 with t-BuLi followed by condensation of the resulting organolithium species with the amide 9 afforded the cyclopropyl ketone 10. Compound 10 was then treated sequentially with LDA and TMSCl to provide a silyl enol ether intermediate (11), which underwent Cope rearrangement to furnish the silyloxy cycloheptadiene 12. Hydrolysis of 12 then resulted in the cycloheptenone 13 as a single stereoisomer in 74% overall yield. 4e). Ring-opening metathesis of the cyclobutene 15 with ethylene in the presence of the ruthenium catalyst 165 proceeded smoothly to provide the cyclooctadiene 18 via Cope rearrangement of the intermediate dialkenyl cyclobutane (17).
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