期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 55, 期 6, 页码 2213-2216出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201510134
关键词
asymmetric catalysis; heterocycles; organocatalysis; self-assembly; synthetic methods
资金
- Welch Foundation [AX-1593]
Both enantiomers of cis- and trans-fused 3,4,4a,8a-tetrahydro-2H,5H-pyrano[2,3-b]pyran-7-carboxylates have been obtained in high diastereoselectivities and enantioselectivities from the same starting materials using a tandem inverse-electron-demand hetero-Diels-Alder/oxa-Michael reaction catalyzed by modularly designed organocatalysts (MDOs). Diastereodivergence was achieved in these reactions through the direct control of the stereochemistry of the bridgehead atoms of the fused ring using new MDOs self-assembled from both enantiomers of proline and cinchona alkaloid thiourea derivatives.
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