Organometallic reactions of. omega.-heterosubstituted N-acyl lactams. A new route to. gamma.-keto aldehydes from 5-ethoxy-2-pyrrolidinone

D Savoia, V Concialini, S Roffia…

Index: Savoia; Concialini; Roffia; Tarsi Journal of Organic Chemistry, 1991 , vol. 56, # 5 p. 1822 - 1827

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Citation Number: 38

Abstract

A new route to yketo aldehydes has been developed in which 5-ethoxy-2-pyrrolidinone is the key intermediate, easily available from 2-pyrrolidinone or succinimide. The lactam undergoes the selective ring opening, previous' in situ" N-acylation reaction with pivaloyl chloride or di-tert-butyl dicarbonate and attack of Grignard reagents or pyridyllithium compounds, whereupon the y-keto aldehydes are produced by acidic hydrolysis. By this ...