双烯酮的有机催化迈克尔环异构化反应：分子内劳乌特-库里尔反应
Organocatalytic Michael cycloisomerization of bis(enones): the intramolecular Rauhut-Currier reaction.
作者信息
Wang Long-Cheng, Luis Ana Liza, Agapiou Kyriacos, Jang Hye-Young, Krische Michael J
机构信息
Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, TX 78712, USA.
出版信息
J Am Chem Soc. 2002 Mar 20;124(11):2402-3. doi: 10.1021/ja0121686.
The utilization of enones as latent enolates enables regioselective enolate formation from chemically robust presursors. In this communication, we report a catalytic Michael cycloisomerization of bis(enones) under Morita-Baylis-Hillman conditions. Upon exposure to 10 mol % tributylphosphine, bis(enone) substrates afford both five- and six-membered ring products. Notably, unsymmetrical bis(enones) possessing sufficient steric or electronic bias yield single isomeric products.
将烯酮用作潜在烯醇盐能够从化学性质稳定的前体中实现区域选择性烯醇盐的形成。在本通讯中，我们报道了在森田-贝利斯-希尔曼条件下双烯酮的催化迈克尔环异构化反应。在暴露于10 mol%的三丁基膦时，双烯酮底物能生成五元环和六元环产物。值得注意的是，具有足够空间位阻或电子偏向的不对称双烯酮能生成单一异构体产物。
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