Catalytic Asymmetric [4+2]-Cycloaddition of Dienes with Aldehydes,Journal of the American Chemical Society

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Catalytic Asymmetric [4+2]-Cycloaddition of Dienes with Aldehydes
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2017-09-25 , DOI: 10.1021/jacs.7b08357
Luping Liu ₁ , Hyejin Kim ₁ , Youwei Xie ₁ , Christophe Farès ₁ , Philip S. J. Kaib ₁ , Richard Goddard ₁ , Benjamin List ₁

Affiliation

Despite its significant potential, a general catalytic asymmetric [4+2]-cycloaddition of simple and electronically unbiased dienes with any type of aldehyde has long been unknown. Previously developed methodologies invariably require activated, electronically engineered substrates. We now provide a general solution to this problem. We show that highly acidic and confined imidodiphosphorimidates (IDPis) are extremely effective Brønsted acid catalysts of the hetero-Diels-Alder reaction of a wide variety of aldehydes and dienes to give enantiomerically enriched dihydropyrans. Excellent stereoselectivity is generally observed and a variety of scents and natural products can be easily accessed.

中文翻译：

二烯与醛的催化不对称[4+2]-环加成反应

尽管具有巨大的潜力，但简单且电子无偏的二烯与任何类型的醛的一般催化不对称 [4+2]-环加成一直是未知的。以前开发的方法总是需要激活的电子工程基板。我们现在为这个问题提供一个通用的解决方案。我们表明，高酸性和受限的亚胺二磷亚胺酯 (IDPis) 是多种醛和二烯的杂狄尔斯-阿尔德反应的极其有效的布朗斯台德酸催化剂，可产生对映异构体富集的二氢吡喃。通常可以观察到出色的立体选择性，并且可以轻松获取各种香味和天然产品。

更新日期：2017-09-25

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