Z-Selective Horner–Wadsworth–Emmons reaction of 2-TOM-cyclopentanone for the synthesis of rac-N-Cbz-Gly-Ψ[(Z)-CF[dbnd]C]-Pro-OH dipeptide isostere.
In: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry, Jg. 55 (2014-11-05), Heft 45, S. 6248-6251
Online
academicJournal
Zugriff:
The Horner–Wadsworth–Emmons reactions of 2-fluoro-2-diethylphosphonoacetic acid with 2-{[(triisopropylsilyl)oxy]methyl}cyclopentanone (2-TOM-cyclopentanone) using methylmagnesium chloride furnished the corresponding tetra-substituted fluoroolefin in a Z -selective manner ( E / Z = 9:91). A facile synthesis of rac - N -Cbz-Gly-Ψ[( Z )-CF C]-Pro-OH as a dipeptide isostere was achieved based on the Z -selective Horner–Wadsworth–Emmons reaction. [ABSTRACT FROM AUTHOR]
| Titel: |
Z-Selective Horner–Wadsworth–Emmons reaction of 2-TOM-cyclopentanone for the synthesis of rac-N-Cbz-Gly-Ψ[(Z)-CF[dbnd]C]-Pro-OH dipeptide isostere.
|
|---|---|
| Autor/in / Beteiligte Person: | Sano, Shigeki ; Matsumoto, Tomoya ; Nanataki, Hiroshi ; Tempaku, Shota ; Nakao, Michiyasu |
| Link: | |
| Zeitschrift: | Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry, Jg. 55 (2014-11-05), Heft 45, S. 6248-6251 |
| Veröffentlichung: | 2014 |
| Medientyp: | academicJournal |
| ISSN: | 0040-4039 (print) |
| DOI: | 10.1016/j.tetlet.2014.09.077 |
| Schlagwort: |
|
| Sonstiges: |
|