An N,N′-Dioxide/In(OTf)3 Catalyst for the Asymmetric Hetero-Diels–Alder Reaction Between Danishefsky's Dienes and Aldehydes: Application in the Total Synthesis of Triketide

Authors

  • Zhipeng Yu,

    1. Key Laboratory of Green Chemistry & Technology (Sichuan University), Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P.R. China, Fax: (+86) 28-8541-8249
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  • Xiaohua Liu,

    1. Key Laboratory of Green Chemistry & Technology (Sichuan University), Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P.R. China, Fax: (+86) 28-8541-8249
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  • Zhenhua Dong,

    1. Key Laboratory of Green Chemistry & Technology (Sichuan University), Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P.R. China, Fax: (+86) 28-8541-8249
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  • Mingsheng Xie,

    1. Key Laboratory of Green Chemistry & Technology (Sichuan University), Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P.R. China, Fax: (+86) 28-8541-8249
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  • Xiaoming Feng Prof. Dr.

    1. Key Laboratory of Green Chemistry & Technology (Sichuan University), Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P.R. China, Fax: (+86) 28-8541-8249
    2. State Key Laboratory of Oral Diseases, Sichuan University, Chengdu 610041, P.R. China
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  • We are grateful to the National Natural Science Foundation of China (grant Nos. 20732003 and 20472056) for financial support. We also thank the Sichuan University Analytical & Testing Center for performing the NMR analysis.

Abstract

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In-teresting catalyst: An asymmetric hetero Diels–Alder reaction between Danishefsky's dienes and various aldehydes using an N,N′-dioxide/In(OTf)3 complex affords highly substituted chiral dihydropyranones with up to 99 % ee (see scheme). The catalyst was applied to the synthesis of triketide from propionaldehyde in 72 % yield and with 97 % ee.

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