Synthesis of alpha-substituted beta-amidophosphines by diastereoselective alkylation. A new access to chiral ligands for asymmetric catalysis

Citation
M. Leautey et al., Synthesis of alpha-substituted beta-amidophosphines by diastereoselective alkylation. A new access to chiral ligands for asymmetric catalysis, J ORG CHEM, 66(16), 2001, pp. 5566-5571
Citations number
27
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
66
Issue
16
Year of publication
2001
Pages
5566 - 5571
Database
ISI
SICI code
0022-3263(20010810)66:16<5566:SOABBD>2.0.ZU;2-9
Abstract
Chiral beta -amidophosphine boranes 7a-f can be diastereoselectively alkyla ted, using O-protected amino-alcohols as chiral inducers, to furnish alpha -substituted beta -amidophosphine boranes 8a-f and 9-12 with up to 72% dias tereoisomeric excess. Selective deprotection afforded optically pure carbox ylic derivative 13 which is a key intermediate for the synthesis of various potential chiral ligands for asymmetric catalysis.