期刊
ORGANIC & BIOMOLECULAR CHEMISTRY
卷 10, 期 14, 页码 2840-2846出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2ob00003b
关键词
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资金
- National Nature Science Foundation of China [20972095, 21172145]
- Science and Technology Commission of Shanghai Municipality [10dz1910105]
- Nippon Chemical Industrial Co., Ltd
- Instrumental Analysis Center of Shanghai Jiao Tong University
Perhydroindolic acids, the by-products obtained in the industrial production of a trandolapril intermediate, were used as chiral organocatalysts in asymmetric Michael addition reactions of aldehydes to nitroolefins. These proline-like catalysts are unique for their rigid bicyclic structure with two H atoms attached to the bridgehead C atoms lying on the opposite side of the ring. They therefore showed high efficiency in asymmetric Michael additions of aldehydes to nitroolefins. Under the optimal conditions, excellent diastereo- and enantioselectivities (up to 99/1 dr and 98% ee) were obtained with high chemical yields for a series of aldehydes and nitroolefins using only 5 mol% catalyst loading. The methodology features easily available catalysts, high catalytic efficiency and environmentally green procedures.
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