Journal of Organic Chemistry p. 4152 - 4156 (1982)
Update date:2022-08-02
Topics:
Hoye, Thomas R.
Caruso, Andrew J.
Magee, Andrew S.
1,1-Dicarbonyl- (ester, ketone, lactone) substituted alkenes are prepared from the corresponding saturated 1-phenylsulfinyl derivatives.These are formed from precursor sulfides, which can be efficiently prepared either by oxidation of β-hydroxy-α-phenylsulfenylcarbonyl compounds or direct acylation of α-phenylsulfenyl enolate anions with acid chlorides.Some of the title compounds can be isolated and then reacted while others are generated and reacted in situ in a Diels-Alder fashion with cyclopentadiene.Endo-exo selectivities are discussed.
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