期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 20, 期 9, 页码 2597-2604出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201304187
关键词
asymmetric synthesis; cycloaddition; enantioselectivity; multicomponent reactions; organocatalysis; ylides
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 of Jiangsu Higher Education Institutions
- Graduate Students Foundation of Jiangsu Normal University [2013YYB123]
A catalytic asymmetric formal [3+3] cycloaddition of 3-indolylmethanol and an in situ-generated azomethine ylide has been established to construct a chiral six-membered piperidine framework with two stereogenic centers. This approach not only represents the first enantioselective cycloaddition of isatin-derived 3-indolylmethanol, but also has realized an unusual enantioselective formal [3+3] cycloaddition of azomethine ylide rather than its common [3+2] cycloadditions. Besides, this protocol combines the merits of a multicomponent reaction and organocatalysis, which efficiently assembles a variety of isatin-derived 3-indolylmethanols, aldehydes, and amino esters into structurally diverse spiro[indoline-3,4-pyridoindoles] with one all-carbon quaternary stereogenic center in high yields and excellent enantioselectivities (up to 93% yield, >99% enantiomeric excess (ee)). Although the diastereoselectivity of the reaction is generally moderate, most of the diastereomers can be separated by using column chromatography followed by preparative TLC.
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