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Asymmetric Mannich-type Reaction Bifunctional Primary Amine-Thiourea-TfOH (BPAToTfOH) as Chiral Phase-Transfer Catalysts: Asymmetric Synthesis of Dihydropyrimidines
Wang Yangyun,Yu Jipan,Miao Zhiwei * #,Chen Ruyu
State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
*Correspondence author
#Submitted by
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Funding: 高等学校博士学科点专项科研基金(No.20070055042)
Opened online:11 January 2011
Accepted by: none
Citation: Wang Yangyun,Yu Jipan,Miao Zhiwei.Asymmetric Mannich-type Reaction Bifunctional Primary Amine-Thiourea-TfOH (BPAToTfOH) as Chiral Phase-Transfer Catalysts: Asymmetric Synthesis of Dihydropyrimidines[OL]. [11 January 2011] http://en.paper.edu.cn/en_releasepaper/content/4404029
 
 
An enantioselective Biginelli reaction has been developed by using a bifunctional primary amine-thiourea-TfOH (BPAToTfOH) as a chiral phase-transfer catalyst and t-BuNH2oTFA as an additive in saturated brine at room temperature. The corresponding dihydropyrimidines were obtained in moderate-to-good yields with up to 99% ee under mild conditions. A plausible transition state has been proposed to explain the origin of the activation and the asymmetric induction.
Keywords:Biginelli reaction; Chiral phase-transfer catalyst; Asymmetric synthesis; Dihydropyrimidines
 
 
 

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