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钯催化的与烯丙醇的级联瓦克/烯丙基化反应序列，生成烯丙基化二氢吡喃酮。

Palladium-Catalyzed Cascade Wacker/Allylation Sequence with Allylic Alcohols Leading to Allylated Dihydropyrones.

作者信息

Huang Wen-Yu, Nishikawa Toshio, Nakazaki Atsuo

机构信息

Graduate School of Bioagricultural Sciences, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8601, Japan.

出版信息

ACS Omega. 2017 Feb 10;2(2):487-495. doi: 10.1021/acsomega.7b00028. eCollection 2017 Feb 28.

DOI:10.1021/acsomega.7b00028
PMID:31457451
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6640993/
Abstract

We describe a cascade Wacker/allylation sequence of β-hydroxy ynones by directly using simple allylic alcohols. This palladium(II)-catalyzed reaction occurs under mild conditions (0 °C to room temperature) and provides a new and efficient synthetic method for the preparation of allylated dihydropyrones. The regiochemical outcomes are consistent with a reaction pathway that includes an insertion/β-OH elimination sequence to form the allylic moiety. A remarkable changeover from allyl to formylethyl products occurs under the simple action of LiBr.

摘要

我们描述了一种通过直接使用简单的烯丙醇对β-羟基炔酮进行级联瓦克/烯丙基化反应序列。这种钯（II）催化的反应在温和条件下（0°C至室温）进行，并为制备烯丙基化二氢吡喃酮提供了一种新的高效合成方法。区域化学结果与包括插入/β-OH消除序列以形成烯丙基部分的反应途径一致。在LiBr的简单作用下，烯丙基产物向甲酰基乙基产物发生了显著转变。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e295/6640993/1a24affc1532/ao-2017-000285_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e295/6640993/63e496cdd987/ao-2017-000285_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e295/6640993/962532e2f4e9/ao-2017-000285_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e295/6640993/d1e2cfdf3075/ao-2017-000285_0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e295/6640993/1a24affc1532/ao-2017-000285_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e295/6640993/63e496cdd987/ao-2017-000285_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e295/6640993/962532e2f4e9/ao-2017-000285_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e295/6640993/d1e2cfdf3075/ao-2017-000285_0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e295/6640993/1a24affc1532/ao-2017-000285_0002.jpg

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