Y. Masuyama et al., IN TURN OR IN REVERSE PALLADIUM-CATALYZED CARBONYL ALLYLATION AND DIELS-ALDER REACTION BY 2-METHYLENE-3-BUTEN-1-OL, Chemistry Letters, (7), 1993, pp. 1199-1202
Using PdCl2(PhCN)2-SnCl2, 2-methylene-3-buten-1-ol causes carbonyl all
ylation of various aldehydes to afford 1-substituted-3-methylene-4-pen
ten-1-ols; the Diels-Alder reaction of those with dienophiles produces
1-(2-hydroxyethyl)cyclohexenes. Diels-Alder reaction of 2-methylene-3
-buten-1-ol with dienophiles followed by carbonyl allylation produces
structurally isomeric 1-methylene-2-(hydroxymethyl)cyclohexanes.