期刊
ORGANIC & BIOMOLECULAR CHEMISTRY
卷 18, 期 20, 页码 3917-3926出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0ob00541j
关键词
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资金
- National Natural Science Foundation of China [NNSFC: 21871237]
An enantioselective Michael/transesterification tandem reaction of alpha-hydroxy indanones with ortho-ester chalcones was realized using dinuclear zinc catalysts. A series of enantiomerically pure spiro[indanone-2,3 '-isochromane-1-one] derivatives were obtained in good yields with excellent stereoselectivities (up to >20 : 1 dr, up to >99% ee). This protocol could be conducted on a gram scale without affecting its stereoselectivities. In addition, the absolute stereochemistry of the products was determined by X-ray crystallographic analysis of 3ac, and a positive nonlinear effect was observed. Finally, a possible catalytic cycle was proposed to explain the origin of the enantioselectivity.
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