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- W2146232324 abstract "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 alpha-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 alpha,alpha-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." @default.
- W2146232324 created "2016-06-24" @default.
- W2146232324 creator A5003686558 @default.
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- W2146232324 date "2001-11-27" @default.
- W2146232324 modified "2023-10-18" @default.
- W2146232324 title "Electrophilic Fluorination of Pyroglutamic Acid Derivatives: Application of Substrate-Dependent Reactivity and Diastereoselectivity to the Synthesis of Optically Active 4-Fluoroglutamic Acids" @default.
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- W2146232324 doi "https://doi.org/10.1021/jo0106804" @default.
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