A temporary-bridge strategy for enantioselective organocatalyzed synthesis of aza-seven-membered rings

作者:Goudedranche Sebastien; Pierrot David; Constantieux Thierry; Bonne Damien*; Rodriguez Jean
来源:Chemical Communications, 2014, 50(98): 15605-15608.
DOI:10.1039/c4cc07731h

摘要

We report the first enantioselective organocatalyzed domino synthesis of azepane moieties. This temporary-bridge strategy is based on a conceptually original annulation of ambident electrophilic and 1,4-bis-nucleophilic alpha-ketoamides with 1,3-bis-electrophilic enals. The obtained oxygen-bridged azepanes can be selectively transformed into optically active azepanone, azepanol or azepanedione derivatives of high synthetic value.

  • 出版日期2014