Flexible, Phase-Transfer Catalyzed Approaches to 4‑Substituted Prolines

A range of 4-substituted prolines can be rapidly synthesized from a protected glycine Schiff base in only four steps and in 27–55% overall yield. Phase transfer catalysis allows direct access to both enantiomeric series, and the relative stereochemistry at the 4-position is readily controlled (>1...

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Bibliographic Details
Published inOrganic letters Vol. 16; no. 18; pp. 4778 - 4781
Main Authors Johnston, Heather J, McWhinnie, Fergus S, Landi, Felicetta, Hulme, Alison N
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.09.2014
Amer Chemical Soc
Subjects
Catalysis
Chemistry
Chemistry, Organic
Glycine - chemistry
Hydrogenation
Molecular Structure
Oligopeptides - pharmacology
Physical Sciences
Proline - analogs & derivatives
Proline - chemical synthesis
Proline - chemistry
Schiff Bases
Science & Technology
Stereoisomerism
ALPHA-AMINO-ACIDS
PEPTIDES
ENANTIOSELECTIVE SYNTHESIS
METATHESIS
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Summary:A range of 4-substituted prolines can be rapidly synthesized from a protected glycine Schiff base in only four steps and in 27–55% overall yield. Phase transfer catalysis allows direct access to both enantiomeric series, and the relative stereochemistry at the 4-position is readily controlled (>10:1 dr) through the choice of hydrogenation conditions.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol502239g