Synthesis of (L)-4-fluorotryptophan

David W. Konas; Drilona Seci; Safa Tamimi

doi:10.1080/00397911.2010.523154

Synthesis of (L)-4-fluorotryptophan

David W. Konas, Drilona Seci, Safa Tamimi

Chemistry and Biochemistry

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

7 Scopus citations

Abstract

A new synthesis of stereochemically pure (L)-4-fluorotryptophan [i.e., (2S)-4-fluorotryptophan] in seven steps from 4-fluoroindole is described. A key reaction in the synthetic strategy is a diastereoselective alkylation of the Schollkopf chiral auxiliary with a fluorinated electrophile. All reaction steps are efficient and proceed in at least 80% yield.

Original language	English
Pages (from-to)	144-152
Number of pages	9
Journal	Synthetic Communications
Volume	42
Issue number	1
DOIs	https://doi.org/10.1080/00397911.2010.523154
State	Published - Jan 2012

Keywords

4-fluorotryptophan
Asymmetric synthesis
fluoroamino acids
organofluorine chemistry

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10.1080/00397911.2010.523154

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abstract = "A new synthesis of stereochemically pure (L)-4-fluorotryptophan [i.e., (2S)-4-fluorotryptophan] in seven steps from 4-fluoroindole is described. A key reaction in the synthetic strategy is a diastereoselective alkylation of the Schollkopf chiral auxiliary with a fluorinated electrophile. All reaction steps are efficient and proceed in at least 80\% yield.",

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AU - Konas, David W.

AU - Seci, Drilona

AU - Tamimi, Safa

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N2 - A new synthesis of stereochemically pure (L)-4-fluorotryptophan [i.e., (2S)-4-fluorotryptophan] in seven steps from 4-fluoroindole is described. A key reaction in the synthetic strategy is a diastereoselective alkylation of the Schollkopf chiral auxiliary with a fluorinated electrophile. All reaction steps are efficient and proceed in at least 80% yield.

AB - A new synthesis of stereochemically pure (L)-4-fluorotryptophan [i.e., (2S)-4-fluorotryptophan] in seven steps from 4-fluoroindole is described. A key reaction in the synthetic strategy is a diastereoselective alkylation of the Schollkopf chiral auxiliary with a fluorinated electrophile. All reaction steps are efficient and proceed in at least 80% yield.

KW - 4-fluorotryptophan

KW - Asymmetric synthesis

KW - fluoroamino acids

KW - organofluorine chemistry

UR - https://www.scopus.com/pages/publications/80052878029

U2 - 10.1080/00397911.2010.523154

DO - 10.1080/00397911.2010.523154

M3 - Article

AN - SCOPUS:80052878029

SN - 0039-7911

VL - 42

SP - 144

EP - 152

JO - Synthetic Communications

JF - Synthetic Communications

IS - 1

ER -

Synthesis of (L)-4-fluorotryptophan

Abstract

Keywords

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