Gold(I)-catalyzed cascade cyclization reaction: highly regio- and diastereoselective intermolecular addition of water and alcohols to epoxy alkynes.

作者信息

Dai Lun-Zhi, Qi Ming-Juan, Shi Yong-Ling, Liu Xu-Guang, Shi Min

机构信息

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai, China 200032.

出版信息

Org Lett. 2007 Aug 2;9(16):3191-4. doi: 10.1021/ol0713640. Epub 2007 Jul 13.

We have developed a novel access to ketal skeletons through a highly regio- and diastereoselective intermolecular addition of water and alcohols to alkynyl epoxides catalyzed by gold(I). This procedure involves a domino three-membered ring-opening, 6-exo-cycloisomerization, and subsequent intra- or intermolecular nucleophilic addition to a double-bond sequence.