Dual catalysis in enantioselective oxidopyrylium-based [5 + 2] cycloadditions.

Dual catalysis in enantioselective oxidopyrylium-based [5 + 2] cycloadditions.
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DOI:
10.1021/ja206997e
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发表时间:
2011-09-21
影响因子:
15
通讯作者:
Jacobsen, Eric N.
Jacobsen, Eric N.
中科院分区:
化学1区
文献类型:
--
作者:
Burns, Noah Z.;Witten, Michael R.;Jacobsen, Eric N.

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报道了一种基于氧化吡喃中间体的催化不对称分子内[5+2]环加成反应的新方法。该双催化剂体系由手性的伯氨基硫脲和次手性的非手性硫脲组成。实验证据表明,每种物种都需要一种新型的协同催化,以生成反应性的吡喃离子对,该对离子对随后进行环加成反应,具有很高的对映体选择性。
A new method is reported for effecting catalytic enantioselective intramolecular [5+2] cycloadditions based on oxidopyrylium intermediates. The dual catalyst system consists of a chiral primary aminothiourea and a second achiral thiourea. Experimental evidence points to a new type of cooperative catalysis with each species being necessary to generate a reactive pyrylium ion pair which undergoes subsequent cycloaddition with high enantioselectivity.
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