TY - JOUR
T1 - Preparation of α-aminophosphines on solid support
T2 - Model studies and parallel synthesis
AU - Ben-Aroya, B. Bar Nir
AU - Portnoy, Moshe
N1 - Funding Information:
This research was supported by the Israel Science Foundation, founded by the Israel Academy of Sciences and Humanities.
PY - 2002/6/17
Y1 - 2002/6/17
N2 - On-resin assembly of phosphine ligands represents a formidable challenge. Following model solution studies, we developed two synthetic routes for α-aminophosphine synthesis on solid support. The ligands are prepared via the Mannich reaction of the resin-bound aldehyde, amine and diphenylphosphine with very good yield and purity. Alternatively, the amine can serve as the anchoring building block. The ligands were qualitatively and quantitatively analyzed using gel-phase 31P and 13C NMR techniques. The studies culminated in the parallel synthesis of a 40-member library of borane-protected α-aminophosphines.
AB - On-resin assembly of phosphine ligands represents a formidable challenge. Following model solution studies, we developed two synthetic routes for α-aminophosphine synthesis on solid support. The ligands are prepared via the Mannich reaction of the resin-bound aldehyde, amine and diphenylphosphine with very good yield and purity. Alternatively, the amine can serve as the anchoring building block. The ligands were qualitatively and quantitatively analyzed using gel-phase 31P and 13C NMR techniques. The studies culminated in the parallel synthesis of a 40-member library of borane-protected α-aminophosphines.
KW - Aminophosphines
KW - Combinatorial chemistry
KW - Mannich reaction
KW - Solid-phase synthesis
UR - http://www.scopus.com/inward/record.url?scp=0037124525&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(02)00471-4
DO - 10.1016/S0040-4020(02)00471-4
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AN - SCOPUS:0037124525
SN - 0040-4020
VL - 58
SP - 5147
EP - 5158
JO - Tetrahedron
JF - Tetrahedron
IS - 25
ER -