Volume 2009, Issue 6 p. 904-911
Full Paper

Synthesis of Substituted 5-(Pyrrolidin-2-yl)tetrazoles and Their Application in the Asymmetric Biginelli Reaction

Yong-Yong Wu

Yong-Yong Wu

Laboratory of Modern Organic Synthetic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. China, Fax: +86-21-64166128

Institute of Organic Chemistry, School of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, P. R. China

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Zhuo Chai

Zhuo Chai

Laboratory of Modern Organic Synthetic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. China, Fax: +86-21-64166128

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Xin-Yuan Liu

Xin-Yuan Liu

Laboratory of Modern Organic Synthetic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. China, Fax: +86-21-64166128

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Gang Zhao

Gang Zhao

Laboratory of Modern Organic Synthetic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. China, Fax: +86-21-64166128

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Shao-Wu Wang

Shao-Wu Wang

Institute of Organic Chemistry, School of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, P. R. China

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First published: 02 February 2009
Citations: 68

Graphical Abstract

A series of chiral substituted 5-(pyrrolidin-2-yl)tetrazoles have been synthesized and evaluated as organocatalysts for the asymmetric Biginelli reaction to provide 3,4-dihydropyrimidin-2(1H)-one (DHPM) derivatives in good yields and moderate enantioselectivities.

Abstract

A series of chiral substituted 5-(pyrrolidin-2-yl)tetrazoles have been synthesized and evaluated as organocatalysts for the asymmetric Biginelli reaction. The relationship between catalytic activity and the different catalyst structures is briefly discussed. By using the optimized catalyst C10 (10 mol-%), a series of 3,4-dihydropyrimidin-2(1H)-one (DHPM) derivatives have been obtained in 63–88 % yields and 68–81 % ee values within 24 h at room temperature. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)