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Structure‐odour correlation, part XIV : Aldol reaction of acyl furans to α, β‐unsaturated furanyl ketones (naginata ketone analogues) and their olfactive properties
Author(s) -
Weyerstahl Peter,
Schulze Matthias
Publication year - 1991
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.2730060302
Subject(s) - chemistry , aldol reaction , enol , ketone , silylation , dehydration , organic chemistry , dehydration reaction , aldol condensation , enol ether , stereochemistry , catalysis , biochemistry
Starting from the acylfurans la‐4a by aldol reaction of the Mukaiyama type the aldols lc, If, 2c, 2e, 2f, 3d, 3f, 4d , were prepared via the silyl enol ethers lb‐4b . Dehydration of the aldols gave the α, β‐unsaturated ketones lg, lj, 2g, 2i, 2j, 3h, 3j . Their olfactive properties are described. The 2‐acyl‐5‐methylfurans 2g, 2i, 2j exhibit the most pleasant odours.