Synlett

Desymmetrization of substituted 1, 3-diketones: A formal synthesis of (+)-stemoamide

N Bogliotti, PI Dalko, J Cossy

Index: Bogliotti, Nicolas; Dalko, Peter I.; Cossy, Janine Synlett, 2006 , # 16 p. 2664 - 2666

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Citation Number: 13

Abstract

The diketoester 3 was synthesized from 2,4-pentanedione (1). After bis-allylation of 1 (NaH, s-BuLi, TMEDA, allylbromide, cyclohexane), [9] compound 2 was obtained in 34% yield (Scheme [2] ). Treatment of 2 with NaH, followed by addition of ethyl bromoacetate furnished an inseparable mixture of the desired monoalkylated compound 3 and the dialkylated product 3′. The mixture of 3/3′ was treated with Noyori's catalyst (R,R)-I, under hydrogen transfer conditions ...