Highly diastereoselective synthesis of tricyclic fused-pyrans by sequential hydride shift mediated double C(sp3)–H bond functionalization†,Chemical Science

当前位置： X-MOL 学术 › Chem. Sci. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Highly diastereoselective synthesis of tricyclic fused-pyrans by sequential hydride shift mediated double C(sp3)–H bond functionalization†
Chemical Science ( IF 7.6 ) Pub Date : 2018-06-25 00:00:00 , DOI: 10.1039/c8sc02103a
Keiji Mori _{1,

2} , Nobuaki Umehara ₁ , Takahiko Akiyama ₁

Affiliation

Described herein is the Brønsted acid-catalyzed double C(sp³)–H bond functionalization of alkyl phenethyl ether derivatives. In this process, a [1,5]-[1,5]-hydride shift occurred successively to afford tricyclic fused pyran derivatives in excellent chemical yields with excellent diastereoselectivities (up to >20 : 1). The key to achieve this reaction was the introduction of two methyl groups at the benzylic position, which was effective in both hydride shift processes: (1) the Thorpe–Ingold effect for the first hydride shift and (2) conformational control in the second hydride shift.

中文翻译：

通过连续氢化物位移介导的双 C(sp3)–H 键功能化高度非对映选择性合成三环稠合吡喃†

本文描述的是布朗斯台德酸催化的烷基苯乙基醚衍生物的双C(sp ³ )-H键官能化。在此过程中，[1,5]-[1,5]-氢化物连续发生转变，以优异的化学收率和优异的非对映选择性（高达％3E20：1）提供三环稠合吡喃衍生物。实现该反应的关键是在苄基位置引入两个甲基，这在两个氢化物转移过程中都有效：（1）第一次氢化物转移的索普-英戈尔德效应和（2）第二次氢化物中的构象控制转移。

更新日期：2018-06-25

点击分享查看原文

点击收藏

公开下载

阅读更多本刊最新论文本刊介绍/投稿指南11