Enantioselective Addition of Diethylzinc to Aromatic Aldehydes Catalyzed by Modular Amino Acids and Phenylethanamine Based Chiral Ligands

doi:10.6023/cjoc1111252

Chin. J. Org. Chem. ›› 0, Vol. 0 ›› Issue (0): 1136-1140.DOI: 10.6023/cjoc1111252

Notes

手性氨基酸酰胺催化二乙基锌与芳香醛不对称加成反应

苟绍华^a,b, 叶仲斌^a,b, 蔡潇潇^b, 刘曼^b, 蒋文超^b

a 西南石油大学油气藏地质及开发工程国家重点实验室成都 610500;
b 西南石油大学化学化工学院成都 610500

收稿日期:2011-11-25 修回日期:2011-12-30 出版日期:2012-06-13 发布日期:2012-02-17
通讯作者: 苟绍华 E-mail:shaohuagou@swpu.edu.cn, shgou@126.com
基金资助:
油气藏地质及开发工程国家重点实验室开放基金(No. PLN1105)资助项目.

Enantioselective Addition of Diethylzinc to Aromatic Aldehydes Catalyzed by Modular Amino Acids and Phenylethanamine Based Chiral Ligands

Gou Shaohua^a,b, Ye Zhongbin^a,b, Cai Xiaoxiao^b, Liu Man^b, Jiang Wenchao^b

a State Key Laboratory of Oil and Gas Reservoir Geology and Exploitation, Southwest Petroleum University, Chengdu 610500;
b School of Chemistry and Chemical Engineering, Southwest Petroleum University, Chengdu 610500

Received:2011-11-25 Revised:2011-12-30 Online:2012-06-13 Published:2012-02-17
Supported by:
Project supported by the Open Fund of Key Laboratory of Oil and Gas Reservoir Geology and Exploitation (No. PLN1105).

Abstract

Enantioselective addition of diethylzinc to a series of aromatic aldehydes was developed by chiral ligand (S)-N-(4-methoxyphenethyl)-3-phenyl-2-(tosylamino)propanamide (1d), which was derivatived from a modular amino acids and long chain amine containg OMe. The catalytic system employing 15 mol% of 1d without using titanium complex was found to promote the addition of diethylzinc (ZnEt₂) to a wide range of aromatic aldehydes with electron-donating and electron- withdrawing substituents, giving up to 87% ee of the corresponding secondary alcohol under mild conditions.

Key words: addition reaction, aldehyde, amino acid, phenylethanamine, ditheylzinc

Cite this article

Gou Shaohua, Ye Zhongbin, Cai Xiaoxiao, Liu Man, Jiang Wenchao. Enantioselective Addition of Diethylzinc to Aromatic Aldehydes Catalyzed by Modular Amino Acids and Phenylethanamine Based Chiral Ligands[J]. Chin. J. Org. Chem., 0, 0(0): 1136-1140.

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手性氨基酸酰胺催化二乙基锌与芳香醛不对称加成反应

Enantioselective Addition of Diethylzinc to Aromatic Aldehydes Catalyzed by Modular Amino Acids and Phenylethanamine Based Chiral Ligands

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