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Enantioselective synthesis and sensory properties of 3‐methylthiodecanal
Author(s) -
Jiang Yaolin,
Liu Hao,
Liu Yongguo,
Yang Shaoxiang,
Sun Baoguo,
Tian Hongyu
Publication year - 2017
Publication title -
flavour and fragrance journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.393
H-Index - 70
eISSN - 1099-1026
pISSN - 0882-5734
DOI - 10.1002/ffj.3370
Subject(s) - enantioselective synthesis , chemistry , octanal , enantiomer , nucleophilic substitution , stereochemistry , mesylate , catalysis , organic chemistry , hexanal
The enantioselective synthesis of two enantiomers of 3‐methylthiodecanal was described, in which the optically active 1‐undecen‐4‐ols prepared by asymmetric catalytic addition of n ‐octanal with allyltributylstannane went through oxidation of double bond and nucleophilic substitution of hydroxy group via mesylate to afford the target molecules with about 90% ee values. Odour properties and approximate thresholds were determined by means of GC/Olfactory. The data indicated that two enantiomers of 3‐methylthiodecanal presented distinctive odour feature from each other and also a slight difference in odour intensity.