Synthesis of sterically hindered 4a, 9a-disubstituted 1, 2, 3, 4, 4a, 9a-hexahydrocarbazoles from4a-methyl-1, 2, 3, 4-tetrahydro-4aH-carbazole with organolithium reagents

✍ Scribed by Jose´Gonzalo Rodri´guez; Anahi´ Urrutia

• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 382 KB
• Volume: 54
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(98)00962-4

✦ Synopsis

The reaction of 4a-methyl-l,2,3,4-tetrahydrocarbazole (1) with organolithium reagents affords the sterically hindered alkyl, aryl or alkenyl cis-4a-methyl-9a-substituted-l,2,3,4,4a,9ahexahydrocarbazole derivatives (2) in excellent yields. Two diastereomeric pairs were isolated for the 9a-see-butyl derivative. Evidence for a radical mechanism is supported by epr.