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用于合成手性γ-羟基醛等效物的酮与丙二烯的线性选择性铜催化还原偶联策略的开发。

Development of a Strategy for Linear-Selective Cu-Catalyzed Reductive Coupling of Ketones and Allenes for the Synthesis of Chiral γ-Hydroxyaldehyde Equivalents.

作者信息

Klake Raphael K, Gargaro Samantha L, Gentry Skyler L, Elele Sharon O, Sieber Joshua D

机构信息

Department of Chemistry , Virginia Commonwealth University , 1001 West Main Street , Richmond , Virginia 23284-3028 , United States.

出版信息

Org Lett. 2019 Oct 4;21(19):7992-7998. doi: 10.1021/acs.orglett.9b02973. Epub 2019 Sep 18.

DOI:10.1021/acs.orglett.9b02973
PMID:31532684
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6781103/
Abstract

We report the development of a stereoselective method for the allylation of ketones utilizing -substituted allyl equivalents generated from a chiral allenamide. By choice of the appropriate ligand for the Cu-catalyst, high linear selectivity can be obtained with good diastereocontrol. This methodology allows access to chiral γ-hydroxyaldehyde equivalents that were applied in the synthesis of chiral γ-lactones and 2,5-disubstitued tetrahydrofurans.

摘要

我们报道了一种立体选择性方法的开发，该方法用于酮的烯丙基化反应，利用从手性烯丙酰胺生成的α-取代烯丙基等效物。通过为铜催化剂选择合适的配体，可以获得高线性选择性并具有良好的非对映体控制。这种方法能够得到手性γ-羟基醛等效物，其可用于手性γ-内酯和2,5-二取代四氢呋喃的合成。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfed/6781103/b9883a061b97/ol9b02973_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfed/6781103/8df77c0ec4b8/ol9b02973_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfed/6781103/17c19e735b77/ol9b02973_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfed/6781103/fdb983504eb6/ol9b02973_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfed/6781103/acc27d86cf2b/ol9b02973_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfed/6781103/1b09747b1874/ol9b02973_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfed/6781103/b9883a061b97/ol9b02973_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfed/6781103/8df77c0ec4b8/ol9b02973_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfed/6781103/17c19e735b77/ol9b02973_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfed/6781103/fdb983504eb6/ol9b02973_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfed/6781103/acc27d86cf2b/ol9b02973_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfed/6781103/1b09747b1874/ol9b02973_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfed/6781103/b9883a061b97/ol9b02973_0006.jpg

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