The Journal of Organic Chemistry

Stereoselective reduction of enantiopure β-enamino esters by hydride: a convenient synthesis of both enantiopure β-amino esters

C Cimarelli, G Palmieri

文献索引：Cimarelli, Cristina; Palmieri, Gianni Journal of Organic Chemistry, 1996 , vol. 61, # 16 p. 5557 - 5563

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被引用次数: 154

摘要

The reduction of enantiopure β-enamino esters 1 with sodium triacetoxyborohydride in acetic acid is described. This occurs with good diastereo-and enantioselectivity to yield β- amino esters 2 and 3 (after hydrogenolysis of the N-chiral group). A model is reported for the origin of the stereoselectivity through an enol ester-diacetoxyborohydride 6, which affords the intramolecular reduction. By choosing the appropriate chiral amine, this procedure ...