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Reversible P(III)/P(V) Redox: Catalytic Aza-Wittig Reaction for the Synthesis of 4(3H)-Quinazolinones and the Natural Product Vasicinone

Authors

  • Long Wang,

    1. Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Central China Normal University, Wuhan, 430079, People's Republic of China, Fax: (+86)-27-6786-2041; phone: (+86)-27-6786-7958
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  • Ying Wang,

    1. Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Central China Normal University, Wuhan, 430079, People's Republic of China, Fax: (+86)-27-6786-2041; phone: (+86)-27-6786-7958
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  • Min Chen,

    1. Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Central China Normal University, Wuhan, 430079, People's Republic of China, Fax: (+86)-27-6786-2041; phone: (+86)-27-6786-7958
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  • Ming-Wu Ding

    Corresponding author
    1. Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Central China Normal University, Wuhan, 430079, People's Republic of China, Fax: (+86)-27-6786-2041; phone: (+86)-27-6786-7958
    • Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Central China Normal University, Wuhan, 430079, People's Republic of China, Fax: (+86)-27-6786-2041; phone: (+86)-27-6786-7958

    Search for more papers by this author

Abstract

The catalytic aza-Wittig reaction based on a phosphine/phosphine oxide catalytic cycle is reported. The by-product triphenylphosphine oxide (Ph3PO) was reduced in situ to triphenylphosphine (Ph3P) with good chemselectivity so that the aza-Wittig reaction can be accomplished by using merely a catalytic amount of triphenylphosphine. The reaction has been demonstrated in an efficient synthesis of 4(3H)-quinazolinones and the natural product (S)-vasicinone in high yields, by using a catalytic amount of triphenylphosphine (5%) and the tetramethyldisiloxane/titanium tetraisopropoxide [TMDS/Ti(O-i-Pr)4] reductant system (81–95% yields and >99% ee).

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