SAMP » - -pyrrolidinamine

An excellent synthetic method for asymmetric C—C-bond formation which gives consistently high enantioselectivity has been developed using azaenolates based on chiral hydrazones. (S)-or (/ )-2-(methoxymethyl)-1 -pyrrolidinamine (SAMP or RAMP) are chiral hydrazines, easily prepared from proline, which on reaction with various aldehydes and ketones yield optically active hydrazones. After the asymmetric 1,4-addition to a Michael acceptor, the chiral auxiliary is removed by ozonolysis to restore the ketone or aldehyde functionality. The enolates are normally prepared by deprotonation with lithium diisopropylamide. 

S)-(+)-4-Methyl-3-heptanone 3-Heptanone, 4-methyl-, (S)- (9) (51532-30-0) 3-Pentanone SAMP-hydrazone 1-Pyrrolidinamine, N-(1-ethyl propylidene)-2-(methoxymethyl)-, (S)- (9) (59983-36-7)... 

Fig. 10.31. Enders SAMP method for the generation of enantiomerically pure a-alkylated carbonyl compounds SAMP, S-aminoprolinol methyl ether = S-2-methoxymethyl-1 -pyrrolidinamine.

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