Journal of Organic Chemistry p. 944 - 947 (1992)
Update date:2022-09-26
Topics:
Beak, Peter
Song, Zhiguo
Resek, James E.
The ene reactions of dimethyl dioxosuccinate (1) and of diethyl dioxosuccinate (2) with olefins give the expected addition products.The reactions of 1 with vinyl ethers or an eneamine provide the cyclopentenones 15 and 16 in a sequence which is consistent with an ene reaction followed by a cyclization.The tin tetrachloride catalyzed conversion of 6 to 17 provides an example of a formal type II ene reaction to give a cyclopentyl ring.However, the stereochemistry of 17 suggests the reaction involves a stepwise ionic process.
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