Nucleophilic additions to a spiro[2,4]hepta-4,6-diene 4-nitrile: Synthesis of 1,2-disubstituted cyclopentenes

✍ Scribed by Jeremy T. Starr; Alain Baudat; Erick M. Carreira

• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 235 KB
• Volume: 39
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(98)01143-5

✦ Synopsis

Organocuprates react with spiro [2,4]heptadiene 4-nitrile to furnish ring-opened cyclopentadiene adducts which can be chemoselectively monohydrogenated to the corresponding unsaturated cyclopentene nitriles. The use of optically active spiro [2,4]heptadiene ,allows for the asymmetric synthesis of chiral cyclopentadienes and cyclopentenes that may serve as useful starting materials for asymmetric synthesis.