Inexpensive reagents for the synthesis of amides from esters and for regioselective opening of epoxides

A Solladie-Cavallo, M Bencheqroun

Index: Solladie-Cavallo, A.; Bencheqroun, M. Journal of Organic Chemistry, 1992 , vol. 57, # 22 p. 5831 - 5834

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Citation Number: 42

Abstract

Lithium aluminum amides [LiAl (NHR),], 6a-6d, easily prepared in EhO or THF from 1 equiv of LiAlH4 yd 5 equiv of amine, proved to be efficient reagents for the synthesis of secondary amides from esters (-100% wlth unhindered amines and 92% with tBuNH2). They also open aryl epoxides with very high regioselectivity to give 97-98% of the 8-amino-a-arylethanols (corresponding to the SNz mechanism).