Site-switchable mono-O-allylation of polyols

Hua Tang, Yu-Biao Tian, Hongyan Cui, Ren-Zhe Li, Xia Zhang and Dawen Niu ()
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Hua Tang: Sichuan University
Yu-Biao Tian: Sichuan University
Hongyan Cui: Sichuan University
Ren-Zhe Li: Sichuan University
Xia Zhang: Sichuan University
Dawen Niu: Sichuan University

Nature Communications, 2020, vol. 11, issue 1, 1-10

Abstract: Abstract Site-selective modification of complex molecules allows for rapid accesses to their analogues and derivatives, and, therefore, offers highly valuable opportunities to probe their functions. However, to selectively manipulate one out of many repeatedly occurring functional groups within a substrate represents a grand challenge in chemistry. Yet more demanding is to develop methods in which alterations to the reaction conditions lead to switching of the specific site of reaction. We report herein the development of a Pd/Lewis acid co-catalytic system that achieves not only site-selective, but site-switchable mono-O-allylation of polyols with readily available reagents and catalysts. Through exchanging the Lewis acid additives that recognize specific hydroxyls in a polyol substrate, our system managed to install a versatile allyl group to the target in a site-switchable manner. Our design demonstrates remarkable scope, and is amenable to the direct derivatization of various complex, bioactive natural products.

Date: 2020
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DOI: 10.1038/s41467-020-19348-x

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