An approach to cyclohepta[b]indoles through an allenamide (4 + 3) cycloaddition-Grignard cyclization-Chugaev elimination sequence.

ABSTRACT: A strategy for synthesizing highly functionalized cyclohepta[b]indoles through a concise (4 + 3) cycloaddition-cyclization-elimination sequence is described. The cycloaddition features nitrogen-stabilized oxyallyl cations derived from epoxidations of N-aryl-N-sulfonyl-substituted allenamides, while the cyclization and elimination employed an intramolecular Grignard addition and a one-step Chugaev process, respectively.

SUBMITTER: He S 

PROVIDER: S-EPMC3998770 | biostudies-literature | 2014 Apr

REPOSITORIES: biostudies-literature