Acid-labile δ-ketal-β-hydroxy esters by asymmetric hydrogenation of corresponding δ-ketal-β-keto esters in the presence of CaCO3

Weizheng Fan; Wanfang Li; Xin Ma; Xiaoming Tao; Xiaoming Li; Ying Yao; Xiaomin Xie; Zhaoguo Zhang

doi:10.1039/C2CC31002C

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Acid-labile δ-ketal-β-hydroxy esters by asymmetric hydrogenation of corresponding δ-ketal-β-keto esters in the presence of CaCO₃†

Weizheng Fan,^a Wanfang Li,^a Xin Ma,^a Xiaoming Tao,^a Xiaoming Li,^a Ying Yao,^a Xiaomin Xie^a and Zhaoguo Zhang*^ab

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* Corresponding authors

^a School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China

^b Shanghai Institute of Organic Chemistry, 345 Lingling Road, Shanghai 200032, China
E-mail: zhaoguo@sjtu.edu.cn

Abstract

A series of acid-labile, optically pure ε-substituted δ-ketal-β-hydroxy esters were obtained by a Ru-SunPhos catalyzed asymmetric hydrogenation of the corresponding ε-substituted δ-ketal-β-keto esters. CaCO₃ played a dual role in the hydrogenation reaction—removing the acid generated during the formation of the catalyst and maintaining the activity of the catalyst.

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Article information

DOI: https://doi.org/10.1039/C2CC31002C
Article type: Communication
Submitted: 11 Feb 2012
Accepted: 28 Feb 2012
First published: 29 Feb 2012

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Chem. Commun., 2012,48, 4247-4249

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Acid-labile δ-ketal-β-hydroxy esters by asymmetric hydrogenation of corresponding δ-ketal-β-keto esters in the presence of CaCO₃

W. Fan, W. Li, X. Ma, X. Tao, X. Li, Y. Yao, X. Xie and Z. Zhang, Chem. Commun., 2012, 48, 4247 DOI: 10.1039/C2CC31002C

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Chemical Communications