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N,O‐heterocycles, 24. Novel approach to the ring‐opening reaction of isoxazolidinium salts to 1,3‐amino alcohols
Author(s) -
Liguori Angelo,
Romeo Giovanni,
Sindona Giovanni,
Uccella Nicola
Publication year - 1988
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19881210116
Subject(s) - chemistry , ring (chemistry) , iodide , lithium iodide , medicinal chemistry , lithium (medication) , yield (engineering) , stereochemistry , polymer chemistry , organic chemistry , medicine , materials science , electrode , electrolyte , metallurgy , endocrinology
Abstract Substituted isoxazolidinium salts 6 – 14 undergo ring‐opening reaction when treated with lithium iodide to yield 1,3‐amino alcohols 15 – 23 having multiple chiral centres. The overall process proceeds through a probable single‐electron‐transfer mechanism with the redox system being the N,O‐heterocyclic cations and the iodide anion.