Organic Chemistry Portal



High Performance of Rh(Phebox) Catalysts in Asymmetric Reductive Aldol Reaction: High Anti-Selectivity

Hisao Nishiyama,* Takushi Shiomi, Yasunori Tsuchiya and Isamu Matsuda

*Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464-8603, Japan, Email:

H. Nishiyama, T. Shiomi, Y. Tsuchiya, I. Matsuda, J. Am. Chem. Soc., 2005, 127, 6972-6973.

DOI: 10.1021/ja050698m

see article for more reactions


Chiral rhodium(bisoxazolinylphenyl) complexes efficiently catalyze the asymmetric reductive aldol reaction of aldehydes and α,β-unsaturated esters with hydrosilanes to give the corresponding β-hydroxypropionates with high anti-selectivity and enantioselectivity. The selectivity is discussed.

see article for more examples

Enantioselective Synthesis of Optically Active 3,3-Diarylpropanoates by Conjugate Hydrosilylation with Chiral Rh-bis(oxazolinyl)phenyl Catalysts

K. Itoh, A. Tsuruta, J.-i. Ito, Y. Yamamoto, H. Nishiyama, J. Org. Chem., 2012, 77, 10914-10919.

Conjugate Reduction of α,β-Unsaturated Aldehydes with Rhodium(bis­oxazolinylphenyl) Catalysts

Y. Kanazawa, H. Nishiyama, Synlett, 2006, 3343-3345.

Key Words

β-Hydroxy Esters, Reductive Aldol Reaction

ID: J48-Y2005-2360