催化对映选择性串联羰基叶立德形成-分子内[3+2]环加成反应的范围
The scope of catalytic enantioselective tandem carbonyl ylide formation-intramolecular [3 + 2] cycloadditions.
作者信息
Hodgson David M, Labande Agnès H, Pierard Françoise Y T M, Expósito Castro María A
机构信息
Department of Chemistry, University of Oxford, South Parks Road, Oxford OX1 3QY, UK.
出版信息
J Org Chem. 2003 Aug 8;68(16):6153-9. doi: 10.1021/jo0343735.
Catalytic enantioselective tandem carbonyl ylide formation-intramolecular 1,3-dipolar cycloaddition reactions of 2-diazo-3,6-diketoesters show promising scope in terms of asymmetric induction as the tethered alkene/alkyne dipolarophile component is varied. Cycloadditions were found to occur in moderate to very good yields, with a difference in ee exhibited by the electronically different 2-diazo-3,6-diketoesters 1, 25 and 33, 34. Values for ee of up to 90% for alkene dipolarophiles and up to 86% for alkyne dipolarophiles were obtained.
2-重氮-3,6-二酮酯的催化对映选择性串联羰基叶立德形成-分子内1,3-偶极环加成反应在不对称诱导方面显示出广阔的前景，因为连接的烯烃/炔烃亲偶极体组分有所不同。发现环加成反应以中等至非常好的产率发生，电子性质不同的2-重氮-3,6-二酮酯1、25以及33、34的对映体过量（ee）存在差异。对于烯烃亲偶极体，ee值高达90%，对于炔烃亲偶极体，ee值高达86%。
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