Tetrahedron p. 3649 - 3660 (1982)
Update date:2022-07-29
Topics:
Verhe, Roland
Kimpe, Norbert De
Courtheyn, Dirk
Buyck, Laurent De
Schamp, Niceas
Treatment of α-acyl-α,β-unsaturated ketones with sulfuric acid or dimethylformamide-hydrogen chloride or p-toluenesulfonic acid gave rise to 3-acyl-2-alkyl-4,5-dihydrofurans.Similar cyclization of α-acyl-α,β-unsaturated esters initially afforded 3-alkoxycarbonyl-2-alkyl-4,5-dihydrofurans which were transformed into 2-acylbutanolides on further reaction with sulfuric acid.This acid catalized cyclization is strongly dependent upon the substitution pattern of the electrophilic alkenes, the acid used and reaction conditions.
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Doi:10.1021/jo00167a018
(1983)Doi:10.1039/b000442l
(2000)Doi:10.1023/A:1012474416163
(2001)Doi:10.3987/COM-05-10482
(2005)Doi:10.1055/s-1995-3977
(1995)Doi:10.1021/jo00168a055
(1983)