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An Investigation into the Allylic Imidate Rearrangement of Trichloroacetimidates Catalysed by Cobalt Oxazoline Palladacycles
Author(s) -
Nomura Hiroshi,
Richards Christopher J.
Publication year - 2007
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/chem.200700873
Subject(s) - chemistry , allylic rearrangement , catalysis , medicinal chemistry , oxazoline , yield (engineering) , cobalt , enantiomeric excess , cyclopentadienyl complex , enantiomer , stereochemistry , enantioselective synthesis , organic chemistry , materials science , metallurgy
Dimeric palladacycles, di‐μ‐X‐bis[{η 5 ‐( S )‐( p R )‐2‐[2′‐(4′‐methylethyl)oxazolinyl]cyclopentadienyl,1‐ C ,3′‐ N }(η 4 ‐tetraphenylcyclobutadiene)cobalt]dipalladium (COP‐X), containing bridging groups X=OAc, Cl, Br, I, O 2 CCF 3 , p ‐O 2 CC 6 H 4 F, were synthesised and compared as catalysts for the asymmetric allylic imidate rearrangement of ( E )‐Cl 3 CC(NH)OCH 2 CHCHR with R= n Pr. The enantiomeric excess of the product ( S )‐Cl 3 CC(O)NHCHRCHCH 2 was essentially invariant of X (93–96 %) and the yield increased in the sequence I< p ‐O 2 CC 6 H 4 F