Premium
A Practical Domino‐ Claisen–Cope Sequence in the Synthesis of New Blooming Citrus and Potent Floral Rose Alcohols
Author(s) -
Liu Jie,
Zou Yue,
Zhou Lijun,
Chai An,
Wang Chao,
Dang HaiShan,
Wang Quanrui,
Goeke Andreas
Publication year - 2017
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201700200
Subject(s) - chemistry , odor , claisen rearrangement , domino , ionone , botany , organic chemistry , stereochemistry , biology , catalysis
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 ).