An expeditious, high-yielding construction of the food aroma compounds 6-acetyl-1,2,3,4-tetrahydropyridine and 2-acetyl-1-pyrroline.
[reaction: see text] The key compound responsible for the aroma of bread, 6-acetyl-1,2,3,4-tetrahydropyridine (1), has been constructed in an efficient three-step procedure from 2-piperidone in an overall yield of 56%. Compound 1 was liberated in the final step under basic conditions. A related synthetic route produced 2-acetyl-1-pyrroline (2), the principal component of cooked rice, in 10% overall yield.
Harrison
Tyler J
TJ
Department of Chemistry, 2036 Main Mall, University of British Columbia, Vancouver, B.C., Canada, V6T 1Z1.
Dake
Gregory R
GR
D005502:Food; D005503:Food Additives / Q000138:chemical synthesis*; D009812:Odorants; D011725:Pyridines / Q000138:chemical synthesis*; D011758:Pyrroles / Q000138:chemical synthesis*
C492489:6-acetyl-1,2,3,4-tetrahydropyridine; D005503:Food Additives; D011725:Pyridines; D011758:Pyrroles; C426303:2-acetyl-1-pyrroline