138871-54-2

Upstream product

• 13154-24-0 triisopropylsilyl chloride 
• 132974-83-5 (5S)-5-[[(tert-butyldiphenylsilyl)oxy]methyl]pyrrolidin-2-one 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 125629-91-6 (S)-5-(hydroxymethyl)-1-(phenylmethyl)-2-pyrrolidinone 
• 100-39-0 benzyl bromide 
• 98-79-3 L-Pyroglutamic acid 
• 4931-66-2 methyl (S)-pyroglutamate 
• 17342-08-4 (S)-Pyroglutaminol 

Downstream Products

• 138871-55-3 (S)-1-Benzyl-5-(tert-butyl-diphenyl-silanyloxymethyl)-3-phenylselanyl-pyrrolidin-2-one 
• 1228469-11-1 (2S,5S)-1,2-dibenzyl-5-((tert-butyldiphenylsilyloxy)methyl)-2-ethylpyrrolidine 
• 1250259-38-1 (S)-1-benzyl-2-((tert-butyldiphenylsilyloxy)methyl)pyrrolidine 

Relevant academic research and scientific papers

Direct, one-pot sequential reductive alkylation of lactams/amides with grignard and Organolithium reagents through lactam/amide activation

(Figure Presented) Be dazzled by the sequence: The first efficient and general one-pot method for the reductive bisalkylation of lactams/ amides with Grignard and organolithium reagents has been developed (see scheme; DTBMP = 2,6-di-tert-butyl-4methylpyridine, Tf=trifluoromethanesulfonyl).

Electrophilic fluorination of pyroglutamic acid derivatives: Application of substrate-dependent reactivity and diastereoselectivity to the synthesis of optically active 4-fluoroglutamic acids

Electrophilic fluorination of enantiomerically pure 2-pyrrolidinones (4) derived from (L)-glutamic acid has been investigated as a method for the synthesis of single stereoisomers of 4-fluorinated glutamic acids. Reaction of the lactam enolate derived from 9 with NFSi results in a completely diastereoselective monofluorination reaction to yield the monocyclic trans-substituted α-fluoro lactam product 21. Unfortunately, a decreased kinetic acidity in 21 and other structurally related monofluorinated products renders them resistant to a second fluorination. In contrast, the bicyclic lactam 12 is readily difluorinated under the standard conditions described to yield the α,α-difluoro lactam 24. The difference in reactivity between the two types of related lactams is attributed mainly to the presence or lack of a steric interaction between the base used for deprotonation and the protecting group present in the pyrrolidinone substrates. This conclusion was reached based on analysis of the X-ray crystal structure of 21, molecular modeling, and experimental evidence. The key intermediates 21 and 24 are converted to (2S,4R)-4-fluoroglutamic acid and (2S)-4,4-difluoroglutamic acid, respectively.