Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University , Nanchong 637002, P. R. China.
Org Lett. 2015 Jan 2;17(1):150-3. doi: 10.1021/ol503383x. Epub 2014 Dec 19.
A palladium-catalyzed (3 + 2) cycloaddition of vinyl cyclopropane and α,β-unsaturated imines generated in situ from aryl sulfonyl indoles is reported. The reaction proceeds with high diastereoselectivity to provide the optically enriched spirocyclopentane-1,3'-indolenines in up to 74% yield and with up to 97% ee, which contains an all-carbon quaternary center and two tertiary stereocenters. The reaction involves a first conjugate addition of the carbon anion of zwitterionic π-allylpalladium complex from vinyl cyclopropane to the in situ formed unsaturated imine followed by a palladium-catalyzed intramolecular C3-allylation of indole.
报道了钯催化的乙烯基环丙烷和芳基磺酰吲哚原位生成的α,β-不饱和亚胺的（3 + 2）环加成反应。该反应具有很高的非对映选择性，以高达 74%的收率和高达 97%的对映选择性提供了光学纯的螺环戊烷-1,3'-吲哚啉，其中包含全碳季碳中心和两个叔立体中心。该反应涉及从乙烯基环丙烷的两性π-烯丙基钯配合物的碳阴离子的第一次共轭加成到原位形成的不饱和亚胺，然后是钯催化的吲哚的 C3-烯丙基化。
