1552271-77-8

Upstream product

• 100-58-3 phenylmagnesium bromide 
• 195964-54-6 1-tert-butyl 2-methyl (2S)-5-methoxypyrrolidine-1,2-dicarboxylate 
• 188200-05-7 1-(tertbutyloxycarbonyl)-5-(hydroxy)pyrrolidine-2-carboxylic acid methyl ester 
• 108963-96-8 (S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one 
• 1552271-24-5 (2S,5S)-1-tert-butyl 2-methyl 5-(naphthalen-1-yl)pyrrolidine-1,2-dicarboxylate 

Downstream Products

• 1552271-85-8 ((2S,2'S,5S,5'S)-1,1'-((2-hydroxy-5-methyl-1,3-phenylene)-bis-(methylene))-bis-(5-(naphthalen-1-yl)pyrrolidine-2,1-diyl))-bis-(diphenylmethanol) 
• 1552271-28-9 [(2S,5S)-5-(naphthalen-1-yl)pyrrolidin-2-yl]diphenylmethanol 

Relevant academic research and scientific papers

A Catalyst Designed for the Enantioselective Construction of Methyl- and Alkyl-Substituted Tertiary Stereocenters

Tertiary methyl-substituted stereocenters are present in numerous biologically active natural products. Reported herein is a catalytic enantioselective method for accessing these chiral building blocks using the Mukaiyama-Michael reaction between silyl ketene thioacetals and acrolein. To enable remote enantioface control on the nucleophile, a new iminium catalyst, optimized by three-parameter tuning and by identifying substituent effects on enantioselectivity, was designed. The catalytic process allows rapid access to chiral thioesters, amides, aldehydes, and ketones bearing an α-methyl stereocenter with excellent enantioselectivities, and allowed rapid access to the C4-C13 segment of (-)-bistramide A. DFT calculations rationalized the observed sense and level of enantioselectivity.

Development of ProPhenol ligands for the diastereo- and enantioselective synthesis of β-hydroxy-α-amino esters

A zinc-ProPhenol-catalyzed direct asymmetric aldol reaction between glycine Schiff bases and aldehydes is reported. The design and synthesis of new ProPhenol ligands bearing 2,5-trans-disubstituted pyrrolidines was essential for the success of this process. The transformation operates at room temperature and affords syn β-hydroxy-α-amino esters in high yields with good to excellent levels of diastereo- and enantioselectivity.