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全取代环丙烷的非对映选择性开环及分子内傅克烷基化反应。

Diastereoselective ring opening of fully-substituted cyclopropanes intramolecular Friedel-Crafts alkylation.

作者信息

Lanke Veeranjaneyulu, Zhang Fa-Guang, Kaushansky Alexander, Marek Ilan

机构信息

Schulich Faculty of Chemistry , Technion - Israel Institute of Technology , Technion City 3200009 , Haifa , Israel . Email:

出版信息

Chem Sci. 2019 Aug 27;10(41):9548-9554. doi: 10.1039/c9sc03832a. eCollection 2019 Nov 7.

DOI:10.1039/c9sc03832a
PMID:32055326
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6979362/
Abstract

We herein disclose a diastereoselective ring opening of non-donor-acceptor cyclopropanes an intramolecular Friedel-Crafts alkylation to functionalized dihydronaphthalene scaffolds possessing quaternary carbon stereocentres. The transformation proceeds through a selective bond breaking at the most alkylated carbon centre with a pure retention of configuration. Mechanistic investigations and computational studies revealed that alkoxy functionality is the key for selective bond breaking leading to a complete retention of configuration.

摘要

我们在此公开了一种非供体-受体环丙烷的非对映选择性开环反应——分子内傅克烷基化反应，用于构建具有季碳立体中心的功能化二氢萘骨架。该转化过程通过在最烷基化的碳中心进行选择性键断裂来实现，构型完全保持。机理研究和计算研究表明，烷氧基官能团是选择性键断裂并导致构型完全保持的关键。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afb1/6979362/122d1d5aa4a5/c9sc03832a-s6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afb1/6979362/96e2c23d0a49/c9sc03832a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afb1/6979362/db00420218cb/c9sc03832a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afb1/6979362/31686342d0a9/c9sc03832a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afb1/6979362/fd5d988ebb4c/c9sc03832a-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afb1/6979362/0d8496c9d792/c9sc03832a-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afb1/6979362/122d1d5aa4a5/c9sc03832a-s6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afb1/6979362/96e2c23d0a49/c9sc03832a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afb1/6979362/db00420218cb/c9sc03832a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afb1/6979362/31686342d0a9/c9sc03832a-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afb1/6979362/fd5d988ebb4c/c9sc03832a-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afb1/6979362/0d8496c9d792/c9sc03832a-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/afb1/6979362/122d1d5aa4a5/c9sc03832a-s6.jpg

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