Helvetica Chimica Acta p. 676 - 687 (1998)
Update date:2022-08-12
Topics:
Rippert, Andreas Johannes
The new, axially chiral bis(4,5-dihydrooxazoles) 4 have been synthesized in a straightforward manner, starting from the substituted, racemic 1,1′-biphenyl-2,2′-dicarboxylic acids 1 and optically active amino alcohols 2. The adducts were resolved by medium-performance liquid chromatography (MPLC; see Scheme 1). Formation of CuI complexes of 4 was followed by 1H-NMR spectroscopy. The catalytic behavior of these complexes has been investigated by asymmetric cyclopropanation of styrene with ethyl diazoacetate. Beside the influence of steric factors, a significant electronic effect on asymmetric induction could also be observed (see Scheme 2 and Table).
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