1-Pyrrolidinamine, 2-

RAMP (R)-l-Amino-2-methoxyraethylpyrrolidine 1-Pyrrolidinamine, 2-(methoxyraethyl)-, (R)- 65, 173, 183 REDUCTION OF CARBOXYLIC ACIDS TO ALDEHYDES. 66, 121 RING EXPANSION, 65, 17... 

S)-(-)-l-AMIN0-2-METH0XYMETHYLPYRR0LIDINE (SAMP) AND (R)-(+)-l-AHIN0-2-METH0XYMETHYLPYRR0LIDINE (RAMP), VERSATILE CHIRAL AUXILIARIES (1-Pyrrolidinamine, 2-(methoxymethyl)-, (S)) (1-Pyrrolidinamine, 2-(methoxymethyl)-, (R))... 

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 SAMP-hydrazone 1-Pyrrolidinamine, N-(l-ethyl-2-methyl pentyl idene)-2-(methoxymethyl)-, [S-[R, R -(Z)]i- (10) (69943-24-4) Propyl iodide Propane, 1-iodo- (8,9) (107-08-4)... 

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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