Citation: Zhi Guo Qiao, Tian Hua Shen, Zhen Fang Fu, Jun Qi Li, Hong Wang, Qing Bao Song. The first catalytic asymmetric addition of diethylzinc to aldehyde promoted by chiral thiourea[J]. Chinese Chemical Letters, ;2011, 22(11): 1265-1268. doi: 10.1016/j.cclet.2011.07.015 shu

The first catalytic asymmetric addition of diethylzinc to aldehyde promoted by chiral thiourea

The State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310032, China

Received Date: 1 April 2011

Fund Project: Open-Ended Fund of the State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology is gratefully acknowledged.

A series of C₂-symmetric and asymmetric chiral thiourea derivatives were synthesized from commercial L-phenylalanine. All of the new compounds have been fully characterized by IR, ¹H NMR, ¹³C NMR, MS spectra and elemental analyses. The chiral thioureas were used as chiral ligands in the catalytic enantioselective ethylation of aldehydes with diethylzinc, the corresponding sec-alcohols were gained with excellent enantioselectivities (up to 87.1% ee) and high yields (up to 76.7%) after the conditions were optimized.
- Chiral thiourea,
- Diethylzinc,
- Amino alcohol,
- C₂-symmetric,
- Enantioselective addition
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