Preparations of Secondary Amines and .beta.-Amino Esters via Additions of Grignard and Reformatsky Reagents to Imines and by One-Pot Reactions of Primary Amines, Aldehydes, and Grignards
作者:Alan R. Katritzky、Qingmei Hong、Zhijun Yang
DOI:10.1021/jo00116a027
日期:1995.6
Additions oi. Grignard and Reformatsky reagents to imines in the presence of 1-(trimethylsilyl)benzotriazole afforded in good yields the corresponding secondary amines and p-amino esters. The procedure is general as imines containing hydrogens a to both carbon and nitrogen can be employed. Extensions of this method to include imines containing other Lewis basic centers, e.g., those derived from furan-, thiophene-, indole-, and p-methoxybenzenecarboxaldehyde, have been successful in avoiding the potential complications which could result from the use of a Lewis acid as the activating : species. The imines need not be isolated, and a one-pot method for the synthesis of secondary amines from aldehydes, primary amines, and Grignard reagents is described.