L. Sun, Pan Li, N. Amankulor
Aug 21, 1998
Citations
0
Influential Citations
12
Citations
Journal
Journal of Organic Chemistry
Abstract
Two practical procedures are described for the synthesis of the N-alkoxy analogues of 3,4,5-trihydroxypiperidine. The key feature of these methods is the intramolecular N-cyclization of hydroxylamine derivatives which are readily obtained from the reduction of the corresponding oximes. One method is to reductively hydroxyaminate an aldehyde group in the presence of a primary tosylated alcohol which is subsequently cyclized in situ upon neutralization. The intramolecular Mitsunobu coupling of a hydroxylamine with a primary alcohol proved useful for the preparation of compounds which contained the trans diol structure.