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通过基团辅助纯化(GAP)化学促进的4-色烯衍生物的不对称[4 + 2]环加成合成。

Asymmetric [4 + 2] cycloaddition synthesis of 4-chromene derivatives facilitated by group-assisted-purification (GAP) chemistry.

作者信息

Rouh Hossein, Tang Yao, Zhang Sai, Ali Ahmed I M, Surowiec Kazimierz, Unruh Daniel, Li Guigen

机构信息

Department of Chemistry and Biochemistry, Texas Tech University Lubbock Texas 79409-1061 USA

出版信息

RSC Adv. 2021 Dec 14;11(63):39790-39796. doi: 10.1039/d1ra08323f. eCollection 2021 Dec 13.

DOI:10.1039/d1ra08323f
PMID:35494146
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9044656/
Abstract

In this work, we present a strategy for the preparation of functionalized 4-chromene derivatives a CsCO-catalyzed [4 + 2] cycloaddition of enantiopure chiral salicyl -phosphonyl imines with allenoates. Fifteen examples were achieved in excellent yields and diastereoselectivity. The products were purified simply by washing the crude mixture with hexanes following the Group-Assisted Purification (GAP) chemistry/technology to bypass traditional separation methods. The absolute configuration was unambiguously determined by X-ray structure analysis.

摘要

在本工作中,我们展示了一种制备官能化4-色烯衍生物的策略——通过碳酸铯催化对映体纯的手性水杨醛-膦酰亚胺与联烯酸酯进行[4+2]环加成反应。以优异的产率和非对映选择性得到了15个实例。按照基团辅助纯化(GAP)化学/技术,通过用己烷洗涤粗混合物,简单地对产物进行了纯化,从而避开了传统的分离方法。通过X射线结构分析明确确定了绝对构型。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b69/9044656/5a9918a255ca/d1ra08323f-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b69/9044656/c072166f8c65/d1ra08323f-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b69/9044656/919537ddeb0a/d1ra08323f-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b69/9044656/973b25a80ce6/d1ra08323f-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b69/9044656/c8e561195fd1/d1ra08323f-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b69/9044656/2a0a71ffa1f4/d1ra08323f-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b69/9044656/89834c9ca864/d1ra08323f-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b69/9044656/5a9918a255ca/d1ra08323f-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b69/9044656/c072166f8c65/d1ra08323f-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b69/9044656/919537ddeb0a/d1ra08323f-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b69/9044656/973b25a80ce6/d1ra08323f-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b69/9044656/c8e561195fd1/d1ra08323f-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b69/9044656/2a0a71ffa1f4/d1ra08323f-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b69/9044656/89834c9ca864/d1ra08323f-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8b69/9044656/5a9918a255ca/d1ra08323f-s5.jpg

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