Regioselectivity of enamines

A major breakthrough in the regioselectivity of enamine reactions followed from the observation by Pfau and Ughetto-Monfrin391 that the cyclohexylamine imine of acetone 191 underwent a,a-bis-alkylation to give 196, in addition to products 195 and 197 derived from self-condensation (Scheme 199). There was no evidence for the formation of the a,a -bis-alkylated product 194. Clearly, as we pointed out in 1982, this can be attributed... 

Hexachloroacetone acts as a source of positive chlorine on reaction with enamines, furnishing, after acid hydrolysis, good yields of a-chloro-ketones. Thus the regioselectivity of enamine formation dictates the regioselectivity of chlorination.Similarly, cyclic enamines react with N2F2 to give the a-fluorocyclo-alkanone after hydrolysis. ... 

---

See also in sourсe #XX -- [ , ]

See also in sourсe #XX -- [ , ]

See also in sourсe #XX -- [ , ]

---