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[2,3]-Sigmatropic Rearrangement of Ynamides: Preparation of α-Amino Allenephosphonates

Authors :
Antoine Fadel
Nicolas Rabasso
Filipe Gomes
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