Pure Appl. Chem., 2008, Vol. 80, No. 4, pp. 743-749
doi:10.1351/pac200880040743
Chiral phenyl-bis(oxazoline) as an efficient auxiliary for asymmetric catalysis*
Hisao Nishiyama, Jun-ichi Ito, Takushi Shiomi, Toru Hashimoto, Takeshi Miyakawa, and Megumi Kitase
Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464-8603, Japan
Abstract:
A new class of phenyl-bis(oxazoline) auxiliaries was readily prepared from isophthaloyl chloride and appropriate β-amino alcohols, and the derived rhodium complexes underwent new cyclization reactions at the metal center and exhibited high catalytic efficiency for asymmetric conjugate reduction of α,β-unsaturated carbonyl compounds and reductive aldol reactions of aldehydes and ketones.
Keywords: asymmetric catalysis; C-H bond activation; oxazoline; reduction; rhodium.
*Paper based on a presentation at the 21st International Congress for Heterocyclic Chemistry (ICHC 21), 15-20 July 2007, Sydney, Australia. Other presentations are published in this issue, pp. 669-805.