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Multigram-scale Synthesis of Enantiopure 3,3-Difluoroproline.

ABSTRACT: An efficient route for the synthesis of enantiopure 3,3-difluoroproline on multigram-scale is described herein. The deoxofluorination can be achieved with DAST on the corresponding racemic pyrrolidinone in good yield. Resolution of the racemate by crystallization with D- and L-tyrosine hydrazide provides both enantiomers of 3,3-difluoroproline in high yield and ee%.

SUBMITTER: Doebelin C

PROVIDER: S-EPMC5456297 | biostudies-literature | 2016 Dec

REPOSITORIES: biostudies-literature

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Multigram-scale Synthesis of Enantiopure 3,3-Difluoroproline.

Doebelin Christelle C He Yuanjun Y Kamenecka Theodore M TM

Tetrahedron letters 20161103 50

An efficient route for the synthesis of enantiopure 3,3-difluoroproline on multigram-scale is described herein. The deoxofluorination can be achieved with DAST on the corresponding racemic pyrrolidinone in good yield. Resolution of the racemate by crystallization with D- and L-tyrosine hydrazide provides both enantiomers of 3,3-difluoroproline in high yield and ee%. ...[more]

PMID: 28584384

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