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: 2001
• Tongue: English
• Weight: 259 KB
• Volume: 2001
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/1099-0690(200111)2001:21<4107::aid-ejoc4107>3.0.co;2-a

✦ Synopsis

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