Selective access to e - And Z -ΔIle-containing peptides via a stereospecific E2 dehydration and an O → N acyl transfer
Organic Letters, ISSN: 1523-7052, Vol: 16, Issue: 15, Page: 4044-4047
2014
- 25Citations
- 15Captures
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Metrics Details
- Citations25
- Citation Indexes25
- CrossRef25
- 22
- Captures15
- Readers15
- 15
Article Description
A concise synthesis of peptides that contain E- or Z-dehydroisoleucine (ΔIle) residues is reported. The key reaction is an unusual anti dehydration of β-tert-hydroxy amino acid derivatives that is mediated by the Martin sulfurane. A subsequent tandem Staudinger reduction-O → N acyl transfer process forges an amide bond to the ΔIle residue with minimal E/Z alkene isomerization. Density functional calculations attribute the stereospecific dehydration to a highly asynchronous E2 anti process. © 2014 American Chemical Society.
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