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ChemInform Abstract: Metalated Epoxides as Carbenoids — Further Advances in the Stereospecific Synthesis of Spirocyclopropanes.

✍ Scribed by Luc Dechoux; Claude Agami; Eric Doris; Charles Mioskowski

Publisher
John Wiley and Sons
Year
2010
Weight
29 KB
Volume
33
Category
Article
ISSN
0931-7597

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The intramolecular cyclopropanation of β,γ-unsaturated metalated epoxides derived from 11 yielded the highly strained tricyclic intermediates 7. The facile hydrolysis of the latter species afforded the α-keto spirocyclopropanes 8 in a stereospecific fashion. Indeed, the stereochemistry of the

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ChemInform Abstract: Metalated Epoxides as Carbenoids. Solvent Effect on the Alkyl 1,2-Shift in α-Hydroxy Epoxide Systems.
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Metalated Epoxides as Carbenoids. Solvent Effect on the Alkyl 1,2-Shift in α-Hydroxy Epoxide Systems. -The BuLi-mediated carbenoid alkyl 1,2-rearrangement of the deuterated α-hydroxy epoxide (I) is investigated in detail. The process is strongly affected by solvation of the lithium atoms, which is