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亲核催化法合成多功能芳基烯丙基醚的不对称合成

Asymmetric synthesis of multifunctional aryl allyl ethers by nucleophilic catalysis.

作者信息

Zhao Shuai, Jin Lei, Chen Zhi-Li, Rui Xue, He Jia-Yi, Xia Ran, Chen Ke, Chen Xiang-Xiang, Yin Zi-Jian, Chen Xin

机构信息

School of Pharmaceutical Engineering & Life Science, Changzhou University Changzhou 213164 P. R. China

出版信息

RSC Adv. 2019 Apr 12;9(20):11585-11588. doi: 10.1039/c9ra00155g. eCollection 2019 Apr 9.

DOI:10.1039/c9ra00155g
PMID:35520223
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9063376/
Abstract

Asymmetric allylic substitution of Morita-Baylis-Hillman (MBH) carbonates with less-nucleophilic phenols mediated by nucleophilic amine catalysis was successfully developed. A variety of substituted aryl allyl ethers were afforded with moderate to high yields with excellent enantioselectivities. The chiral MBH alcohol could be easily accessed from the corresponding aryl allyl ether.

摘要

通过亲核胺催化成功实现了用亲核性较弱的酚对Morita-Baylis-Hillman（MBH）碳酸酯进行不对称烯丙基取代反应。以中等至高产率得到了各种取代的芳基烯丙基醚，且对映选择性优异。相应的芳基烯丙基醚可轻松制得手性MBH醇。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9bb/9063376/b811531606d6/c9ra00155g-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9bb/9063376/854024abc978/c9ra00155g-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9bb/9063376/c22ad8c67b3e/c9ra00155g-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9bb/9063376/b811531606d6/c9ra00155g-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9bb/9063376/854024abc978/c9ra00155g-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9bb/9063376/c22ad8c67b3e/c9ra00155g-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9bb/9063376/b811531606d6/c9ra00155g-s2.jpg

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本文引用的文献

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Synthesis of Both Enantiomers of Chiral Phenylalanine Derivatives Catalyzed by Cinchona Alkaloid Quaternary Ammonium Salts as Asymmetric Phase Transfer Catalysts.手性苯丙氨酸衍生物的对映异构体的全合成，由金鸡纳生物碱季铵盐作为不对称相转移催化剂催化。
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钯催化的科尔比烯醇酯与 MBH 碳酸酯的不对称烯丙基烷基化反应：对映选择性地构建季碳 C-F 氧化吲哚。
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Development of an Acrylate Derivative Targeting the NLRP3 Inflammasome for the Treatment of Inflammatory Bowel Disease.开发一种针对 NLRP3 炎性小体的丙烯酸盐衍生物，用于治疗炎症性肠病。
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Palladium-Catalyzed Asymmetric Construction of Vicinal Tertiary and All-Carbon Quaternary Stereocenters by Allylation of β-Ketocarbonyls with Morita-Baylis-Hillman Adducts.钯催化的通过β-酮羰基与 Morita-Baylis-Hillman 加合物的烯丙基化反应构建偕二取代的三级和全碳季碳中心的对映选择性。
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