An Approach to Cyclohepta[b]indoles through an Allenamide (4+3) Cycloaddition-Grignard Cyclization-Chugaev Elimination Sequence

作者:He Shuzhong; Hsung Richard P*; Presser William R; Ma Zhi Xiong; Haugen Bryan J
来源:Organic Letters, 2014, 16(8): 2180-2183.
DOI:10.1021/ol5006455

摘要

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.

  • 出版日期2014-4-18