1440775-40-5

Basic information

• Product Name: (2S,5S)-2-benzyl 5-phenylpyrrolidine-2-carboxylate
• Synonyms: (2S,5S)-2-benzyl 5-phenylpyrrolidine-2-carboxylate
• CAS NO: 1440775-40-5
• Molecular Weight: 281.354
• Mol File: 1440775-40-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2S,5S)-2-benzyl 5-phenylpyrrolidine-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,5S)-2-benzyl 5-phenylpyrrolidine-2-carboxylate(1440775-40-5)
• EPA Substance Registry System: (2S,5S)-2-benzyl 5-phenylpyrrolidine-2-carboxylate(1440775-40-5)

Safety Data

• Hazardous Substances Data: 1440775-40-5(Hazardous Substances Data)

Upstream product

• 100-58-3 phenylmagnesium bromide 
• 331949-31-6 benzyl (2S)-N-tert-butoxycarbonyl-5-methoxypyrrolidine-2-carboxylate 
• 100-44-7 benzyl chloride 
• 113400-36-5 benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate 
• 98-79-3 L-Pyroglutamic acid 
• 94885-52-6 benzyl (L)-pyroglutamate 

Relevant articles and documents

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.