Alkylation of. alpha.-formamido ketone enolate anions. A versatile synthesis of. alpha.-alkyl. alpha.-amino ketones

J Ackrell, JM Muchowski, E Galeazzi…

Index: Ackrell, Jack; Muchowski, Joseph M. Journal of Organic Chemistry, 1986 , vol. 51, # 17 p. 3374 - 3376

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Citation Number: 22

Abstract

The formamides 7 were rapidly (1 h) cleaved with methanolic hydrogen bromide (10 equiv) at reflux temperature. Thus, the a-benzyl compounds 8 (R= Ph, 3, 4-OCH20CeH3, PhCH2CH2; R'= PhCH2) were isolated as the crystalline hydrobromide salts in 94%, 95%, and 77% yields, respectively. Inasmuch as the a-formamido ketones 6 are easily prepared in three steps from the bromo ketones 3 (see Scheme I and the Experimental Section), the ...