An Approach to Cyclohepta[<i>b</i>]indoles
through an Allenamide (4 + 3) Cycloaddition–Grignard Cyclization–Chugaev
Elimination Sequence
- Publication date
- Publisher
Abstract
A strategy
for synthesizing highly functionalized cyclohepta[<i>b</i>]indoles through a concise (4 + 3) cycloaddition–cyclization–elimination
sequence is described. The cycloaddition features nitrogen-stabilized
oxyallyl cations derived from epoxidations of <i>N-</i>aryl-<i>N-</i>sulfonyl-substituted allenamides, while the cyclization
and elimination employed an intramolecular Grignard addition and a
one-step Chugaev process, respectively