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[2,3]-Sigmatropic Rearrangement of Ynamides: Preparation of α-Amino Allenephosphonates
- Source :
- The Journal of Organic Chemistry. 77:5439-5444
- Publication Year :
- 2012
- Publisher :
- American Chemical Society (ACS), 2012.
-
Abstract
- α-Amino allenephosphonates were easily prepared in two steps from protected amines, propargyl alcohols, and chlorophosphites. First, ynamides were synthesized from unprotected 1-bromopropargyl alcohols using a copper(II) catalyzed coupling reaction. In the second step, the previously prepared ynamides were transformed directly to allenes through a [2,3]-sigmatropic rearrangement of propargyl phosphites. This efficient method led to the formation of a series of α-amino allenephosphonates with diverse substituents on the amine, the phosphonate, and the allene moieties.
Details
- ISSN :
- 15206904 and 00223263
- Volume :
- 77
- Database :
- OpenAIRE
- Journal :
- The Journal of Organic Chemistry
- Accession number :
- edsair.doi.dedup.....9f1aa1f20966ba6d400a3a08b7ac5c59