Synthesis of l-4,4-difluoroglutamic acid via electrophilic difluorination of a lactam

David Konas, James K. Coward

Research output: Contribution to journalArticle

40 Citations (Scopus)

Abstract

(matrix presented) An enantiomerically pure bicyclic lactam proved to be an excellent substrate for electrophilic difluorination using N-fluorobenzenesulfonimide. The resulting difluorinated lactam can be easily converted into L-4,4-difluoroglutamic acid. To the best of our knowledge, this is the first example of a synthetically useful electrophilic difluorination of an unactivated lactam.

Original languageEnglish
Pages (from-to)2105-2107
Number of pages3
JournalOrganic Letters
Volume1
Issue number13
StatePublished - 30 Dec 1999

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Lactams
acids
synthesis
matrices
Substrates
4,4-difluoroglutamic acid

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abstract = "(matrix presented) An enantiomerically pure bicyclic lactam proved to be an excellent substrate for electrophilic difluorination using N-fluorobenzenesulfonimide. The resulting difluorinated lactam can be easily converted into L-4,4-difluoroglutamic acid. To the best of our knowledge, this is the first example of a synthetically useful electrophilic difluorination of an unactivated lactam.",
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Synthesis of l-4,4-difluoroglutamic acid via electrophilic difluorination of a lactam. / Konas, David; Coward, James K.

In: Organic Letters, Vol. 1, No. 13, 30.12.1999, p. 2105-2107.

Research output: Contribution to journalArticle

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AU - Coward, James K.

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N2 - (matrix presented) An enantiomerically pure bicyclic lactam proved to be an excellent substrate for electrophilic difluorination using N-fluorobenzenesulfonimide. The resulting difluorinated lactam can be easily converted into L-4,4-difluoroglutamic acid. To the best of our knowledge, this is the first example of a synthetically useful electrophilic difluorination of an unactivated lactam.

AB - (matrix presented) An enantiomerically pure bicyclic lactam proved to be an excellent substrate for electrophilic difluorination using N-fluorobenzenesulfonimide. The resulting difluorinated lactam can be easily converted into L-4,4-difluoroglutamic acid. To the best of our knowledge, this is the first example of a synthetically useful electrophilic difluorination of an unactivated lactam.

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