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Totally Regio‐ and Stereoselective P–O‐to‐P–C Rearrangement in the Synthesis of Chiral P ‐( o ‐Hydroxyaryl)diazaphospholidine P ‐Oxides
Author(s) -
Legrand Olivier,
Brunel Jean Michel,
Buono Gérard
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199905)1999:5<1099::aid-ejoc1099>3.0.co;2-r
Subject(s) - chemistry , regioselectivity , stereoselectivity , structural isomer , stereochemistry , nuclear magnetic resonance spectroscopy , rearrangement reaction , walden inversion , medicinal chemistry , organic chemistry , catalysis
The totally regio‐ and stereoselective P–O‐to‐P–C rearrangement in the synthesis of various chiral P ‐( o ‐hydroxyaryl)diazaphospholidine P ‐oxides has been investigated. This reaction proceeds with excellent yields ranging from 72 to 92%, total retention of configuration at the phosphorus atom, and complete regioselectivity. An exception was found with naphthyl derivatives, which gave mixtures of two regioisomers. In all cases, the products generated have been unambiguously characterized by 1 H‐, 13 C‐, and 31 P‐NMR spectroscopy as well as by X‐ray‐diffraction analysis.