Iodine - catalyzed prins cyclization of aliphatic and aromatic ketones

Journal of the Brazilian Chemical Society

Reddy, K. R. Kishore K.¹  Silva Jr, Luiz F.¹  Universidade de São Paulo, São Paulo, Brazil¹ 

关键词: iodine;    Prins cyclization;    ketones;    pyrans;    spiro compounds;   

DOI  :  10.5935/0103-5053.20130178

学科分类：化学（综合）

来源: SciELO

【 摘 要 】

Iodine-catalyzed Prins cyclization of homoallylic alcohols and ketones was investigated. Anhydrous conditions and inert atmosphere are not required in this metal-free protocol. The reaction of 2-(3,4-dihydronaphthalen-1-yl)propan-1-ol with six aliphatic symmetric ketones gave the desired products in 67-77% yield. Cyclization was performed with four aliphatic unsymmetric ketones, leading to corresponding pyrans in 66-76% yield. Prins cyclization was also accomplished with four aromatic ketones in 37-66% yield. Finally, Prins cyclization of the monoterpene isopulegol and acetone was successfully achieved.

【 授权许可】

Unknown