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J Org Chem. 2005 Dec 23;70(26):10872-4.

An expeditious, high-yielding construction of the food aroma compounds 6-acetyl-1,2,3,4-tetrahydropyridine and 2-acetyl-1-pyrroline.

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  • 1Department of Chemistry, 2036 Main Mall, University of British Columbia, Vancouver, B.C., Canada, V6T 1Z1.


[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.

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