Bifunctional AgOAc-catalyzed asymmetric [3 + 2] cycloaddition of azomethine ylides.

Bifunctional AgOAc-catalyzed asymmetric [3 + 2] cycloaddition of azomethine ylides.
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DOI:
10.1055/s-2005-921679
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发表时间:
2005-10
期刊:
影响因子:
5.2
通讯作者:
W. Zeng;Yong‐Gui Zhou
W. Zeng;Yong‐Gui Zhou
中科院分区:
化学1区
文献类型:
--
作者:
W. Zeng;Yong‐Gui Zhou

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[反应:见正文] 使用二茂铁基恶唑啉衍生的 N,P 配体开发了双功能 AgOAc 催化的偶氮甲碱叶立德与缺电子烯烃的不对称环加成反应。反应性金属结合的偶氮甲碱叶立德偶极子是通过乙酸酯去质子化形成的,不需要额外的碱。反应以高对映选择性进行。该方法为制备光学活性吡咯烷衍生物提供了一条高效、便捷的途径。
[reaction: see text] A bifunctional AgOAc-catalyzed asymmetric cycloaddition of azomethine ylides with electronic-deficient alkenes was developed using ferrocenyloxazoline-derived N,P ligands. The reactive metal-bound azomethine ylide dipole is formed by the deprotonation with acetate, and extra base is not necessary. The reactions proceed with high enantioselectivity. This method provides an efficient and convenient route to optically active pyrrolidine derivatives.