63007-26-1Relevant articles and documents
A Practical Domino-Claisen–Cope Sequence in the Synthesis of New Blooming Citrus and Potent Floral Rose Alcohols
Liu, Jie,Zou, Yue,Zhou, Lijun,Chai, An,Wang, Chao,Dang, Hai-Shan,Wang, Quanrui,Goeke, Andreas
, (2017/12/01)
Fifty years after its first discovery by Alan Francis Thomas, we describe a versatile, metal and pressure-free domino-Claisen–Cope rearrangement using the readily available α,β-unsaturated aldehydes 5 or their acetals 5′ and allylic alcohols 6. This transformation provides a convenient access to a large number of radiant citrus and floral rosy odorants. Odor profiles of novel floral rosy and citrus alcohols 13, 14, and 16 were studied. Compound 14ba has a floral, rosy, geranium-like character and shows unique performance and diffusiveness. Compound 16ba has a clear main citrus odor character with a clean green grapefruit/rhubarb connotation. Both odorants have been successfully introduced to perfumery recently as Rosyfolia (14ba) and Pomelol (16ba).