126397-41-9Relevant academic research and scientific papers
THE DIELS-ALDER REACTION OF 3-ACETOXY-1-VINYLCYCLOHEXENE WITH METHYL VINYL KETONE
Kawamata, Takeshi,Harimaya, Kenzo,Iitaka, Yoichi,Inayama, Seiichi
, p. 2307 - 2309 (2007/10/02)
The Diels-Alder reaction of 3-acetoxy-1-vinylcyclohexene (1c) with methyl vinyl ketone (MVK) at 110 and 150 deg C gave predominantly the adducts 1-acetoxy-8-acetyl-8aβH-4a(5)-octalin, 3b(8βH) and 3a(8αH), respectively, along with other minor adducts.The stereochemistry of 3a was independently confirmed by X-ray crystallographic analysis of the p-bromobenzoate (3e) derived from 1-desacetyl-3a(3d).The predominant approach of the dienophile (MVK) to 1c was found to have occured anti to the allylic acetate group, contrary to the empirical rule proposed recently.Keywords Diels-Alder reaction; 3-acetoxy-1-vinylcyclohexene; 1-acetoxy-8- acetyl-8aβH-4a(5)-octalin; temperature dependence; X-ray crystallography; endo-selectivity; face-selectivity; anti-addition
