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Sidechain Functionalizations by Cuprate Additions to Phosphorylallenyl‐Substituted Arenetricarbonylchromium Complexes
Author(s) -
Ansorge Markus,
Polborn Kurt,
Müller Thomas J. J.
Publication year - 1999
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/(sici)1099-0682(19990202)1999:2<225::aid-ejic225>3.0.co;2-r
Subject(s) - chemistry , protonation , regioselectivity , cuprate , stereochemistry , medicinal chemistry , ion , crystallography , organic chemistry , catalysis , superconductivity , physics , quantum mechanics
The cuprate addition to (arene)Cr(CO) 3 ‐substituted phosphorylallenes 1 gives rise to the regioselective formation of complexed allylphosphane oxide derivatives 3a – c and allylphosphonate derivatives 3d–j in good yields. In the case of racemic planar chiral ortho ‐substituted complexed (arylallenyl)phosphonates 1c , d the protonation of the intermediate allyl anion proceeds diastereoselectively due to the hindered rotation around the C ipso –C α bond. This diastereoselective protonation is discussed on the basis of the conformational analysis as deduced from the X‐ray structure analyses of the allenylphosphonate 1d and the allylphosphonates 3i , j .