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钯催化脱羧烯丙基化/Wittig 反应:C-乙烯基糖苷的底物控制合成。

Palladium-Catalyzed Decarboxylative Allylation/Wittig Reaction: Substrate-Controlled Synthesis of C-Vinyl Glycosides.

机构信息

Division of Chemistry and Biological Chemistry Nanyang Technological University , School of Physical & Mathematical Sciences, 21 Nanyang Link, Singapore 637371, Singapore.

出版信息

Org Lett. 2017 Jan 20;19(2):416-419. doi: 10.1021/acs.orglett.6b03697. Epub 2017 Jan 8.

Abstract

A palladium-catalyzed one-pot Tsuji-Trost type decarboxylative allylation/Wittig reaction has been developed to synthesize C-vinyl glycosides. Screening of various aldehydes led to formation of β,(E)-selective C-vinyl glycosides with pyridyl group containing aldehydes and β,(Z)-selective C-vinyl glycosides with nonpyridyl aldehydes. A plausible mechanism is proposed based on the coordination effect of the aldehydes.

摘要

钯催化一锅法 Tsuji-Trost 型脱羧烯丙基化/Wittig 反应已被开发用于合成 C-乙烯基糖苷。对各种醛的筛选导致含有吡啶基的醛形成β,(E)选择性的 C-乙烯基糖苷,而不含吡啶基的醛形成β,(Z)选择性的 C-乙烯基糖苷。基于醛的配位效应,提出了一个合理的机制。

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