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Totally Stereoselective P–O to P–C Migration Rearrangement: Application to the Synthesis of New Chiral o ‐Hydroxyaryl Phosphine Oxides
Author(s) -
Legrand Olivier,
Brunel Jean Michel,
Constantieux Thierry,
Buono Gérard
Publication year - 1998
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/(sici)1521-3765(19980615)4:6<1061::aid-chem1061>3.0.co;2-v
Subject(s) - phosphine , stereoselectivity , pseudorotation , chemistry , medicinal chemistry , walden inversion , phosphorus , stereochemistry , organic chemistry , catalysis , ring (chemistry)
A novel class of chiral o ‐hydroxyaryl phosphine oxides such as 1 and 2 has been synthesized by a migration–rearrangement reaction with retention of the configuration at the phosphorus atom. On the basis of experimental results, the mechanism is proposed to be addition–pseudorotation–elimination.