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Synthesis of α-Necrodol:  Unexpected Formation of a Cyclopropene

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journal contribution
posted on 21.03.1997, 00:00 by Douglass F. Taber, Han Yu
Significant 1,3-induction in intramolecular alkylidene C−H insertion is reported. Thus, exposure of ketone I to the lithium salt of (trimethylsilyl)diazomethane provides a 2.4:1.0 ratio of IIa and IIIa, which are deprotected to α-necrodol IIb and the epimeric IIIb. The 1,3-insertion product cyclopropene IV was also formed.