Amidoacetone enolate anions: alkylation and Michael reaction

✍ Scribed by Thomas R. Hoye; Steven R. Duff; Rita S. King

• Publisher: Elsevier Science
• Year: 1985
• Tongue: French
• Weight: 264 KB
• Volume: 26
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)98657-x

✦ Synopsis

The lithium enolate derived from benmmi&scetone ( 1) an be regiospecifically dkylated at Ct 1) and stereospecifically &fed in conjug8te feshion to cyclohexenone without resorting to protection of the free NH. Comparison is ma& with alkyiati~sof methyl hippur8t8. Several years ago&& and coworkers reported1 the enolate anion static and subsaquent trimet~lsi~~~ol ether formation from en extensive series of a-aminoketones. Under kinetic conditions most of these substrates, all of which contained fully su~t~tut~ a-nitr~ atoms, geve r~ioj~~i~ mixtures of enoiates ruing from 5: 1 to 1: 1, We ere interested in the potential use of the enolates of aminoscetone derivatives, including those which still contain an NH (i.e., WHNCH@CH3), in wrbon-c8rbon bond forming re&ions and have therefore carried out the studies described here. flenzamidoacetone ( 112 (from H2NCH2CHOHCH3 + PhCOCl then Jones oxidstion), which upon deprotonation mtainssix