The synthesis of a number of beta-amino tertiary alcohols has been achieved via ring-opening of an unsymmetrical epoxide with primary and secondary amines. The results revealed that primary amines give symmetrical triol products following an undesired acyl migration reaction, whereas secondary amines give the desired chiral (racemic) products. Furthermore, we demonstrate that asymmetric products can be formed using enantiomerically pure epoxide and aromatic amines without any loss of enantiomeric excess.
The synthesis of N-substituted symmetrical azetidines has been achieved in high yields via the reaction of primary amines undergoing an epoxide ring-opening reaction followed by an in situ ring-closing step.
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Synthesis of 1,3-Disubstituted Azetidines via a Tandem Ring-Opening Ring-Closing Procedure. -Treatment of epoxide (I) with primary amines results in formation of the expected azetidines. When secondary amines are employed, symmetrical diamines are produced. -(MARCH-CORTIJOS, A.; SNAPE*, T. J.; TURNER, N. J.; Synlett 2012, 10, 1511-1515, http://dx.doi.org/10.1055/s-0031-1291014 ; Sch. Pharm. Pharm. Sci., Univ. Cent. Lancashire, Preston, Lancashire PR1 2HE, UK; Eng.) -Mais 40-119
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