A catalytic enantioselective route to cis- and trans-3,4,4,5-tetrasubstituted cyclohexanones; remarkable chiral catalyst control in sequential catalytic 1,4-additions to cyclohexadienones
R. Imbos et al., A catalytic enantioselective route to cis- and trans-3,4,4,5-tetrasubstituted cyclohexanones; remarkable chiral catalyst control in sequential catalytic 1,4-additions to cyclohexadienones, TETRAHEDRON, 57(13), 2001, pp. 2485-2489
Asymmetric copper-phosphoramidite catalysed conjugate addition of Et2Zn to
easily accessible, nearly enantiomerically pure cyclohexenones 2 and 4 was
performed. Depending on the enantiomer of the chiral phosphoramidite used,
the cis- or trans-3,4,4,5-tetrasubstituted cyclohexanones 5 and 6 could be
formed selectively. Surprisingly, there is no directing effect of the 5-eth
yl- or 4-alkoxy-substituents and the stereochemical outcome is only governe
d by the configuration of the chiral ligand. (C) 2001 Published by Elsevier
Science Ltd.