3-羟基-4-吡喃酮衍生氧化吡咯啉𬭩叶立德的催化对映选择性分子间[5 + 2]偶极环加成反应。
Catalytic Enantioselective Intermolecular [5 + 2] Dipolar Cycloadditions of a 3-Hydroxy-4-pyrone-Derived Oxidopyrylium Ylide.
机构信息
Department of Chemistry, Rutgers University , Newark, New Jersey 07102, United States.
Department of Chemistry, Brooklyn College, The City University of New York , Brooklyn, New York 11210, United States.
出版信息
Org Lett. 2017 Dec 1;19(23):6356-6359. doi: 10.1021/acs.orglett.7b03196. Epub 2017 Nov 17.
Abstract
The first catalytic enantioselective [5 + 2] dipolar cycloaddition of a 3-hydroxy-4-pyrone-derived oxidopyrylium ylide is described. These studies leveraged the recently recognized ability of oxidopyrylium dimers to serve as the source of ylide, which was found to be key to increasing yields and achieving enantiomeric excesses up to 99%. General reaction conditions were identified for an array of α,β-unsaturated aldehyde dipolarophiles. Reaction products possess four stereocenters, and subsequent reduction introduced a fifth contiguous stereocenter with total stereocontrol.
摘要
首次描述了 3-羟基-4-吡喃酮衍生的氧化吡咯烷二价阳离子叶立德的催化对映选择性 [5 + 2] 偶极环加成反应。这些研究利用了氧化吡咯烷二聚体作为叶立德来源的新能力，这被发现是提高产率和达到高达 99%对映体过量的关键。确定了一系列α,β-不饱和醛双烯的一般反应条件。反应产物具有四个立体中心，随后的还原引入了第五个连续的立体中心，具有总立体控制。
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