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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| Published in | Organic letters Vol. 16; no. 18; pp. 4778 - 4781 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
19.09.2014
Amer Chemical Soc |
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| Abstract | 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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| AbstractList | 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. |
| Author | Johnston, Heather J McWhinnie, Fergus S Landi, Felicetta Hulme, Alison N |
| AuthorAffiliation | University of Edinburgh EaStCHEM School of Chemistry |
| AuthorAffiliation_xml | – name: EaStCHEM School of Chemistry – name: University of Edinburgh |
| Author_xml | – sequence: 1 givenname: Heather J surname: Johnston fullname: Johnston, Heather J – sequence: 2 givenname: Fergus S surname: McWhinnie fullname: McWhinnie, Fergus S – sequence: 3 givenname: Felicetta surname: Landi fullname: Landi, Felicetta – sequence: 4 givenname: Alison N surname: Hulme fullname: Hulme, Alison N email: Alison.Hulme@ed.ac.uk |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/25191962$$D View this record in MEDLINE/PubMed |
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| Keywords | ALPHA-AMINO-ACIDS PEPTIDES ENANTIOSELECTIVE SYNTHESIS METATHESIS |
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| Snippet | 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... 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... |
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| SubjectTerms | 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 |
| Title | Flexible, Phase-Transfer Catalyzed Approaches to 4‑Substituted Prolines |
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