Enantioselective synthesis and sensory properties of 3‐methylthiodecanal | Zendy

Jiang Yaolin | Zendy; Liu Hao | Zendy; Liu Yongguo | Zendy; Yang Shaoxiang | Zendy; Sun Baoguo | Zendy; Tian Hongyu | Zendy

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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.

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