170642-58-7

Upstream product

• 5497-76-7 L-proline tert-butyl ester hydrochloride 
• 100-52-7 benzaldehyde 
• 147-85-3 L-proline 
• 2812-46-6 proline tert-butyl ester 
• 90741-31-4 (S)-N-benzyl-5-thioxoproline tert-butyl ester 
• 16881-39-3 (S)-2-tert-butyl-1-benzylpyrrolidine-1,2-dicarboxylate 
• 100-44-7 benzyl chloride 

Downstream Products

• 1291079-07-6 (R,E)-tert-butyl 1-benzyl-2-(2'-tosylvinyl)pyrrolidine-2-carboxylate 
• 1291079-42-9 (R)-tert-butyl 1-benzyl-2-vinylpyrrolidine-2-carboxylate 
• 1291079-44-1 (1-benzyl-2-vinylpyrrolidin-2-yl)methanol 
• 161564-07-4 (1-benzyl-2-ethylpyrrolidin-2-yl)methanol 
• 31795-93-4 N-benzyl-L-proline 

Relevant academic research and scientific papers

Asymmetric Synthesis of Cα-Substituted Prolines through Curtin–Hammett-Controlled Diastereoselective N-Alkylation

Asymmetric synthesis of α-substituted proline derivatives has been accomplished by an efficient chirality-transfer method. High diastereoselectivity of the N-alkylation of the proline ester (C→N chirality transfer) was achieved when a 2,3-disubstituted be

Ring-Strain Effects in Base-Induced Sommelet–Hauser Rearrangement: Application to Successive Stereocontrolled Transformations

The base-induced Sommelet–Hauser (S–H) rearrangement of azetidine-2-carboxylic acid ester-derived ammonium salts into 2-aryl-substituted derivatives was demonstrated. The ring-strain of four-membered N-heterocycles enables efficient generation of the desired ylide intermediate and enhances the rate of the S–H rearrangement. The asymmetric version of the rearrangement was characterized by excellent levels of successive chirality transmissions. The regio- and stereo-controlled nucleophilic ring opening of the rearrangement products produced quaternary α-aryl amino acid esters with excellent enantiopurities.

Asymmetric α-2-tosylvinylation of in situ-generated N-2-tosylvinyl proline-derived ammonium ylides

Asymmetric α-2-tosylvinylation of N-substituted proline esters using ethynyl tolyl sulfone as an electrophile was shown to proceed in good yield with high enantioselectivities without the addition of any bases. The reaction proceeds via the formation of N-2-tosylvinyl ammonium ylides.

Asymmetric [1,2] Stevens rearrangement of (S)-N-benzylic proline-derived ammonium salts under biphasic conditions

The Stevens rearrangement of (S)-N-benzylic proline-derived ammonium salt with cesium hydroxide in 1,2-dichloroethane is shown to proceed with a high degree of the N-to-C chirality transmission to afford the α-substituted proline derivatives in high enantio-purities. Copyright

Carbapenem biosynthesis: Confirmation of stereochemical assignments and the role of CarC in the ring stereoinversion process from L-Proline

(5R)-Carbapen-2-em-3-carboxylic acid is the simplest structurally among the naturally occurring carbapenem β-lactam antibiotics. It co-occurs with two saturated (3S,5S)- and (3S,5R)-carbapenam carboxylic acids. Confusion persists in the literature about t