Silyl Controlled Asymmetric Mannich Reactions

Enders D, Oberborsch S, Adam J (2000) a-Silyl controlled asymmetric Mannich reactions of acyclic ketones with imines. Synlett 2000 644—646... 

Enders D, Adam J, Oberborsch S, Ward D (2002b) Asymmetric Mannich reactions by a-silyl controlled aminomethylation of ketones. Synthesis 2002 2737-2748... 

Asymmetric Mannich-type reactions provide useful routes for the synthesis of enantiomerically enriched P-amino ketones or esters [48a, 48b]. For the most part, these methods involve the use of chirally modified enolates or imines. Only a handful of examples has been reported on the reaction of imines with enolates of carboxylic acid derivatives or silyl ketene acetals in the presence of a stoichiometric amount of a chiral controller [49a, 49b, 49c]. Reports describing the use of a substoichiometric amount of the chiral agent are even more scarce. This section contains some of the most recent advances in the field of catalytic enantioselective additions of lithium enolates and silyl enol ethers of esters and ketones to imines. 

---