A modular rearrangement approach toward medicinally relevant phosphinic structures.
An unprecedented coupling of a P-C and a C-C bond-forming event in a practical operation was developed to access medicinally relevant phosphinic structures. The strategy relies on an Ireland-Claisen rearrangement triggered by the phospha-Michael addition of silyl phosphonites to allyl acrylates. This protocol was extended to a more versatile three-component variant that utilizes phosphinic acids, acryloyl chlorides, and allylic alcohols as starting materials.
Rogakos
Vassilis
V
Department of Chemistry, Laboratory of Organic Chemistry, University of Athens, Panepistimiopolis Zografou 15771, Athens, Greece.
Georgiadis
Dimitris
D
Dive
Vincent
V
Yiotakis
Athanasios
A
D000179:Acrylates / Q000737:chemistry; D002244:Carbon / Q000737:chemistry; D008511:Medicine; D010721:Phosphinic Acids / Q000737:chemistry* / Q000494:pharmacology; D010758:Phosphorus / Q000737:chemistry
D000179:Acrylates; D010721:Phosphinic Acids; D010758:Phosphorus; D002244:Carbon