期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 24, 期 23, 页码 6277-6281出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201800585
关键词
asymmetric synthesis; dearomatization; diastereoselectivity; dienamine; furfural; ortho-quinodimethane
资金
- NSFC [21772126]
The dearomatizative dienamine-type ortho-quinodimethane species are smoothly generated between 2-alkyl-3-furfurals and chiral secondary amine catalysts, which undergo asymmetric benzylic allylic alkylation reactions with 2-nitroallylic acetates efficiently. A spectrum of densely functionalized 3-furfural derivatives are delivered in moderate to high yields with good to excellent diastereo- and enantioselectivity (up to 98% yield, >19:1 d.r., >99% ee). The latent transformations allow the facile production of some enantioenriched architectures, such as 1,1,2,2-tetraarylethanes and triarylmethanes, which are not easily available from other protocols.
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