| Autor: |
Loach RP; Department of Chemistry, Massachusetts Institute of Technology , 77 Massachusetts Avenue 18-292, Cambridge, Massachusetts 02139, United States., Fenton OS, Amaike K, Siegel DS, Ozkal E, Movassaghi M |
| Jazyk: |
angličtina |
| Zdroj: |
The Journal of organic chemistry [J Org Chem] 2014 Nov 21; Vol. 79 (22), pp. 11254-63. Date of Electronic Publication: 2014 Nov 10. |
| DOI: |
10.1021/jo502062z |
| Abstrakt: |
A versatile strategy for C7-selective boronation of tryptophans, tryptamines, and 3-alkylindoles by way of a single-pot C2/C7-diboronation-C2-protodeboronation sequence is described. The combination of a mild iridium-catalyzed C2/C7-diboronation followed by an in situ palladium-catalyzed C2-protodeboronation allows efficient entry to valuable C7-boroindoles that enable further C7-derivatization. The versatility of the chemistry is highlighted by the gram-scale synthesis of C7-boronated N-Boc-L-tryptophan methyl ester and the rapid synthesis of C7-halo, C7-hydroxy, and C7-aryl tryptophan derivatives. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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