Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China.
Org Lett. 2013 Jan 4;15(1):204-7. doi: 10.1021/ol3032285. Epub 2012 Dec 21.
The self-condensation of alkynals was for the first time implemented under mild organocatalytic conditions and was successfully linked with a domino organocatalytic inverse-electron-demand oxa-Diels-Alder reaction, which led to the development of a facile one-pot method to produce a wide variety of polysubstituted chiral 3,4-dihydropyrans with good to high yields and diastereoselectivities and high enantioselectivities. The unprecedented alkynal self-condensation was revealed to pass through secondary amine-catalyzed C-C triple bond hydration and subsequent aldol condensation.
炔醛的自缩合反应首次在温和的有机催化条件下实现，并成功与多组分的多米诺有机催化反电子需求的氧化烯 Diels-Alder 反应偶联，从而开发出一种简便的一锅法，以高产率和高对映选择性得到多种取代的手性 3,4-二氢吡喃。前所未有的炔醛自缩合反应被揭示是通过二级胺催化的 C-C 三键水合和随后的羟醛缩合反应进行的。
