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

Chemical Communications Pub Date: 2014-10-31 DOI: 10.1039/C4CC07731H

Abstract

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 α-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.

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