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Catalyst-Driven Scaffold Diversity: Selective Synthesis of Spirocycles, Carbazoles and Quinolines from Indolyl Ynones.

ABSTRACT: Medicinally relevant spirocyclic indolenines, carbazoles and quinolines can each be directly synthesised selectively from common indolyl ynone starting materials by catalyst variation. The high yielding, divergent reactions all proceed by an initial dearomatising spirocyclisation reaction to generate an intermediate vinyl-metal species, which then rearranges selectively by careful choice of catalyst and reaction conditions.

SUBMITTER: Liddon JT

PROVIDER: S-EPMC5084754 | biostudies-literature | 2016 Jun

REPOSITORIES: biostudies-literature

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Catalyst-Driven Scaffold Diversity: Selective Synthesis of Spirocycles, Carbazoles and Quinolines from Indolyl Ynones.

Liddon John T R JT James Michael J MJ Clarke Aimee K AK O'Brien Peter P Taylor Richard J K RJ Unsworth William P WP

Chemistry (Weinheim an der Bergstrasse, Germany) 20160519 26

Medicinally relevant spirocyclic indolenines, carbazoles and quinolines can each be directly synthesised selectively from common indolyl ynone starting materials by catalyst variation. The high yielding, divergent reactions all proceed by an initial dearomatising spirocyclisation reaction to generate an intermediate vinyl-metal species, which then rearranges selectively by careful choice of catalyst and reaction conditions. ...[more]

PMID: 27124236

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