Two-Step Formal [3+2] Cycloaddition of Enones/Enals and Allenyl MOM Ether: Gold-Catalyzed Highly Diastereoselective Synthesis of Cyclopentanone Enol Ether Containing an All-Carbon Quaternary Center
作者:Xiaogen Huang、Liming Zhang
DOI:10.1021/ja0717717
日期:2007.5.1
A two-step, highlydiastereoselectiveformal [3+2] cycloaddition between allenyl MOM ether and an enal/enone is developed. Au activation of allenyl ethers is proposed to yield all-carbon 1,3-dipoles, which can undergo concerted intramolecular 1,3-dipolar cycloadditions. Synthetically useful cyclopentanone enol ethers containing an all-carbon quaternary center can be readily prepared with excellent
开发了烯基 MOM 醚和烯醛/烯酮之间的两步、高度非对映选择性的正式 [3+2] 环加成反应。建议对烯基醚进行 Au 活化以产生全碳 1,3-偶极子,其可以进行协同的分子内 1,3-偶极环加成。合成有用的环戊酮烯醇醚含有全碳季中心,可以很容易地制备,并具有优异的非对映控制。