65651-52-7

Upstream product

• 59983-39-0 (S)-1-amino-2-(methoxymethyl)pyrrolidine 
• 67-64-1 acetone 

Downstream Products

• 128572-44-1 (E)-2-acetonylcyclohexanecarboxylate 
• 89393-62-4 5-[(Z)-(S)-2-Methoxymethyl-pyrrolidin-1-ylimino]-3-phenyl-hexanoic acid methyl ester 
• 89393-62-4 (R)-5-[(E)-(S)-2-Methoxymethyl-pyrrolidin-1-ylimino]-3-phenyl-hexanoic acid methyl ester 
• 89393-62-4 (R,S)-1-<<3-phenyl-4-(carboxymethyl)-1-methylbutylidene>amino>-2-(methoxymethyl)pyrrolidine 
• 175430-80-5 (+)-(2S,3'S)-1-<2'-(t-Butyldimethylsilyl)-1'-phenylbut-3'-ylideneamino>-2-methoxymethylpyrrolidine 

Relevant academic research and scientific papers

Regio-, Diastereo-, and Enantioselective Synthesis of vic-Diols via α-Silyl Ketones According to the SAMP/RAMP Hydrazone Method

α-Silylated ketones 5 or 10 of high enantiomeric purity (ee>=90percent) are easily available by silylation or silylation/alkylation of ketones 1 or 6, resp., according to the SAMP/RAMP hydrazone method.Reduction of 5 or 10 with L-selectride, followed by oxidative cleavage of the C-Si bond, leads to vic-diols 11-13 with high diastereoselectivity (de>=90percent) and without racemization.The stereoselectivity of the reduction depends on the structure of the α-silyl ketones 5 or 10, the reducing reagents, and the solvents used.Key Words: Ketones, α-silyl / vic-Diols, diastereo- and enantioselective synthesis / SAMP/RAMP Hydrazones / L-Selectride reductions

Asymmetric Michael Additions via SAMP-/RAMP-Hydrazones Enantioselective 1,4-Addition of Methyl Ketones to Knoevenagel Acceptors

Asymmetric Michael addition of lithiated methyl ketone SAMP-hydrazones (S)-2 to 2-benzylidenemalonates and -dinitriles 3 followed by oxidative cleavage of the 1,4-adducts (SR)-4 by ozonolysis affords 2-substituted 4-oxo diesters and -dinitriles (R)-5 in good overall yields of 50-82percent and high enantiomeric excesses (ee >/= 95percent).

ASYMMETRIC SYNTHESIS OF β-SUBSTITUTED δ-KETOESTERS VIA MICHAEL-ADDITIONS OF SAMP/RAMP-HYDRAZONES TO α,β-UNSATURATED ESTERS, VIRTUALLY COMPLETE 1.6-ASYMMETRIC INDUCTION

A simple and efficient 3-step asymmetric synthesis of β-substituted δ-ketoesters 3 in 45-62percent overall chemical yield and >=96-ca.100percent ee is described.The key step is an asymmetric Michael-addition of lithiated methylketone-SAMP- or RAMP-hydrazones to α,β-unsaturated esters 2 with virtually complete 1.6-asymmetric induction.