Carbon-carbon bond formation between enone and ester carbonyl group induced by samarium diiodide.

[摘要]：Reductive cyclization of Me, TBDMS, C6F5, CH2CCl3, or MOM ester of 4-(2-methyl-6-oxocyclohex-1-enyl)butanoate was attempted by treatment with SmI2, with or without additive (MeOH, H2O, HMPA, NiI2), to establish whether Claisen-type C-C bond formation occurred. The Me ester afforded dimeric products, while the CH2CCl3 and MOM esters yielded hexahydronaphthalenediones. The C6F5 ester gave a spiro compd. All these products were assumed to be formed through an anionic intermediate produced by 2-electron redn. of the enone moiety by SmI2.

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