175430-70-3

Upstream product

• 2550-26-7 4-Phenyl-2-butanone 
• 59983-39-0 (S)-1-amino-2-(methoxymethyl)pyrrolidine 

Downstream Products

• 175430-75-8 (+)-(2S)-1-<1'-(t-Butyldimethylsilyl)-4'-phenylbut-2'-ylideneamino>-2-methoxymethylpyrrolidine 
• 107300-18-5 (2S,2''R)-1-[N-methoxycarbonyl-N-(1-methyl-3-phenylpropyl)amino]-2-(methoxymethyl)pyrrolidine 
• 175430-91-8 (+)-(2S,2'S)-1-<2'-(t-Butyldimethylsilyl)-5'-phenylpent-3'-ylideneamino>-2-methoxymethylpyrrolidine 
• 175431-08-0 (S)-4-(tert-Butyl-dimethyl-silanyl)-1-phenyl-pentan-3-one 

Relevant academic research and scientific papers

Organocerium additions to proline-derived hydrazones: Synthesis of enantiomerically enriched amines

The addition of organocerium reagents (from both organolithium and organomagnesium precursors) to chiral aldehyde hydrazones prepared from 1-aminoproline derivatives has been studied. The additions proceed in good yield and high diastereoselectivity and with good nucleophile (Me, n-Bu, i-Pr, t-Bu, Ph, etc.) and substrate scope (alkyl, alkenyl and aryl). The resulting hydrazines can be converted to amines by N-N bond cleavage through hydrogenolysis (Raney nickel) or by acylation and cleavage with Li/NH 3. The influence of the side chain on the diastereoselectivity was investigated through variation of the substituents to include more coordinating atoms (oxygen and nitrogen) as well as the removal of coordinating atoms. The SAMEMP auxiliary bearing a 2-methoxyethoxymethyl group gave the highest diastereoselectivities. Remarkably, auxiliaries bearing simple methyl and isobutyl substituents gave high selectivities as well. Hypotheses for the origin of the selectivity are presented.

Diastereo- and enantioselective synthesis of δ2-1,2,4-oxadiazolines by 1,3-dipolar cycloaddition of nitrile oxides with chiral hydrazones

Diastereo- and enantioselective 1,3-dipolar cycloadditions of nitrile oxides (3) with α,β-unsaturated hydrazones (2) gave spiro oxadiazolines (4) in good yields and low to excellent diastereomeric excesses (de = 5 - ≥98%). Open chain hydrazones (6) afforded 5,5-disubstituted Δ2-1,2,4-oxadiazolines (7). A subsequent N-N bond cleavage to remove the chiral auxiliary was achieved with formic acid and gave the oxadiazolines (8) (ee = 0 - 91%).