Goudedranche Sébastien, Pierrot David, Constantieux Thierry, Bonne Damien, Rodriguez Jean
Aix Marseille Université, CNRS, Centrale Marseille, ISM2 UMR 7313, 13397, Marseille, France.
Chem Commun (Camb). 2014 Dec 21;50(98):15605-8. doi: 10.1039/c4cc07731h. Epub 2014 Oct 31.
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.
我们报道了氮杂环庚烷部分的首例对映选择性有机催化多米诺合成。这种临时桥连策略基于一种概念新颖的环化反应，即双亲电和亲双烯体的α-酮酰胺与1,3-双亲电烯醛发生环化反应。所得到的氧桥连氮杂环庚烷可选择性地转化为具有高合成价值的旋光氮杂环庚烷酮、氮杂环庚烷醇或氮杂环庚烷二酮衍生物。
