Highly diastereoselective Claisen rearrangement leading to vicinal quaternary carbons construction of oxindoles

作者：Matsuta Yumiko; Kobari Takayuki; Kurashima Sachiko; Kumakura Yuhsuke; Shinada Masashi; Higuchi Kazuhiro; Kawasaki Tomomi^*

来源：Tetrahedron Letters, 2011, 52(46): 6199-6202.

DOI：10.1016/j.tetlet.2011.09.059

• Olefination
• Isomerization
• Cascade reactions
• Spirooxindoles

An efficient approach to spirocyclic oxindole architecture with vicinal quaternary carbon centers is described. The reaction of 2-allyloxyindolin-3-ones with cyanomethylphosphonate at low reaction temperature proceeds smoothly with consecutive olefination, isomerization, deacylation, and anion-accelerated Claisen rearrangement to give the 3,3-disubstituted oxindoles with vicinal quaternary all-carbon centers in high yield and diastereoselectivity. The oxindoles are readily converted into more synthetically advanced spiro-products.

• 出版日期2011-11-16