Reversible P(III)/P(V) Redox: Catalytic Aza-Wittig Reaction for the Synthesis of 4(3H)-Quinazolinones and the Natural Product Vasicinone
Reversible P(III)/P(V) Redox: Catalytic Aza-Wittig Reaction for the Synthesis of 4(3H)-Quinazolinones and the Natural Product Vasicinone
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DOI：
10.1002/adsc.201300950
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发表时间：
2014-03
影响因子：
5.4
通讯作者：
L. Wang;Ying Wang;Min Chen;M. Ding
中科院分区：
文献类型：
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作者：
L. Wang;Ying Wang;Min Chen;M. Ding
报道了基于膦/氧化膦催化循环的催化氮杂维蒂希反应。副产物三苯基膦氧化物（Ph3PO）被原位还原为三苯基膦（Ph3P），具有良好的化学选择性，因此仅使用催化量的三苯基膦即可完成氮杂维蒂希反应。该反应已被证明可以通过使用催化量的三苯基膦 (5%) 和四甲基二硅氧烷/四异丙醇钛 [TMDS/Ti(O-i-Pr)4] 还原剂系统（产率 81-95%）高效合成 4(3H)-喹唑啉酮和天然产物 (S)-vasicinone，且收率高 和 >99%ee）。
The catalytic aza‐Wittig reaction based on a phosphine/phosphine oxide catalytic cycle is reported. The by‐product triphenylphosphine oxide (Ph3PO) was reducedin situto 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).