期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 20, 期 36, 页码 11382-11389出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201402485
关键词
asymmetric synthesis; bispirooxindoles; enantioselectivity; multicomponent reactions; organocatalysis
资金
- National Natural Science Foundation of China [21372002, 21232007]
- Open Foundation of Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials [K201314]
- PAPD
- QingLan Project of Jiangsu Province
The first catalytic asymmetric construction of a new class of bispirooxindole scaffold-containing tetrahydro-beta-carboline moiety has been established through chiral phosphoric acid-catalyzed three-component cascade Michael/Pictet-Spengler reactions of isatin-derived 3-indolylmethanols, isatins, and amino-ester, which afforded structurally complex and diverse bispirooxindoles with one quaternary and one tetrasubstituted stereogenic centers in excellent stereoselectivities (all >95:5 diastereomeric ratio (d.r.), up to 98:2 enantiomeric ratio (e.r.)). This intriguing class of chiral bispirooxindoles integrated the two important structures of tetrahydro-beta-carboline and bispirooxindole, both of them possessing significant bioactivities. This approach also combined the merits of asymmetric organocatalysis and multicomponent tandem reaction, which provided a unique strategy for the preparation of structurally rigid bispiro-architectures with concomitant creation of multiple quaternary stereogenic centers.
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