Synthesis of Substituted 5-(Pyrrolidin-2-yl)tetrazoles and Their Application in the Asymmetric Biginelli Reaction
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
Search for more papers by this authorZhuo 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
Search for more papers by this authorXin-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
Search for more papers by this authorGang 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
Search for more papers by this authorShao-Wu Wang
Institute of Organic Chemistry, School of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, P. R. China
Search for more papers by this authorYong-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
Search for more papers by this authorZhuo 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
Search for more papers by this authorXin-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
Search for more papers by this authorGang 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
Search for more papers by this authorShao-Wu Wang
Institute of Organic Chemistry, School of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, P. R. China
Search for more papers by this authorGraphical Abstract
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)
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