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Diastereoselective Synthesis of New P‐Stereogenic ( ortho ‐Hydroxyaryl)diazaphospholidine–Borane Complexes by a Totally Stereoselective P–O to P–C Migration Rearrangement
Author(s) -
Ngono Christian J.,
Constantieux Thierry,
Buono Gérard
Publication year - 2006
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/ejoc.200500844
Subject(s) - stereocenter , borane , chemistry , stereoselectivity , stereochemistry , walden inversion , enantioselective synthesis , medicinal chemistry , organic chemistry , catalysis
Abstract The totally diastereoselective synthesis of new P‐stereogenic ( o ‐hydroxyaryl)diazaphospholidines, in the form of their borane complexes 4a – 4h , is described. The efficiency of this procedure is based both, on a one‐pot and totally diastereoselective synthesis of the precursors ( ortho ‐bromoaryloxy)diazaphosphospholidine–borane complexes 3a – 3h , and on a stereoselective P–O to P–C migration rearrangement. A X‐ray diffraction study of the structures of the product 4f and his precursor 3f shows unambiguously the totally stereoselectivity of the P–O to P–C rearrangement with clean retention of the phosphorus configuration.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)