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手性螺环丙烷化对醌甲川用铵叶立德。

Enantioselective Spirocyclopropanation of para-Quinone Methides Using Ammonium Ylides.

机构信息

Institute of Organic Chemistry, Johannes Kepler University Linz , Altenbergerstr. 69, 4040 Linz, Austria.

出版信息

Org Lett. 2017 May 5;19(9):2338-2341. doi: 10.1021/acs.orglett.7b00869. Epub 2017 Apr 20.

DOI:10.1021/acs.orglett.7b00869
PMID:28425286
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5420312/
Abstract

The use of Cinchona alkaloid-based chiral ammonium ylides allows for the first highly enantioselective and broadly applicable spirocyclopropanation reactions of para-quinone methides. This strategy provides a straightforward protocol toward the chiral spiro[2.5]octa-4,7-dien-6-one skeleton, which is a frequently found structural motif in important biologically active molecules.

摘要

基于金鸡纳生物碱手性铵叶立德的使用，实现了对 para-醌甲醚的首例高对映选择性和广泛适用的螺环丙二烯反应。该策略提供了一种直接的方法来获得手性螺[2.5]辛-4,7-二烯-6-酮骨架，这是在重要生物活性分子中经常发现的结构基序。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbf7/5423701/32745ef93b8b/ol-2017-00869t_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbf7/5423701/4f2ca1ad17de/ol-2017-00869t_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbf7/5423701/d6a6aa9bb4f9/ol-2017-00869t_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbf7/5423701/32745ef93b8b/ol-2017-00869t_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbf7/5423701/4f2ca1ad17de/ol-2017-00869t_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbf7/5423701/d6a6aa9bb4f9/ol-2017-00869t_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbf7/5423701/32745ef93b8b/ol-2017-00869t_0003.jpg

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