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

David W. Konas; James K. Coward

doi:10.1021/ol991150l

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

David W. Konas
, James K. Coward

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

54 Scopus citations

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 language	English
Pages (from-to)	2105-2107
Number of pages	3
Journal	Organic Letters
Volume	1
Issue number	13
DOIs	https://doi.org/10.1021/ol991150l
State	Published - 30 Dec 1999

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

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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journal = "Organic Letters",

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T1 - Synthesis of l-4,4-difluoroglutamic acid via electrophilic difluorination of a lactam

AU - Konas, David W.

AU - Coward, James K.

PY - 1999/12/30

Y1 - 1999/12/30

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.

UR - https://www.scopus.com/pages/publications/0033619849

U2 - 10.1021/ol991150l

DO - 10.1021/ol991150l

M3 - Article

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SN - 1523-7060

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JO - Organic Letters

JF - Organic Letters

IS - 13

ER -

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

Abstract

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