An Asymmetric Dehydrogenative Diels-Alder Reaction for the Synthesis of Chiral Tetrahydrocarbazole Derivatives

An Asymmetric Dehydrogenative Diels-Alder Reaction for the Synthesis of Chiral Tetrahydrocarbazole Derivatives

An asymmetric dehydrogenative Diels-Alder reaction of 2-methyl-3-phenylmethylindoles and α,β-unsaturated aldehydes has been established. The successful in situ generation of the indole ortho-quinodimethane intermediate and the iminium activation of enals are the keys to success, providing various te...

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Veröffentlicht in:Organic letters 2018-01, Vol.20 (1), p.32-35
Hauptverfasser: Wu, Xiang, Zhu, Hai-Jie, Zhao, Shi-Bao, Chen, Shu-Sen, Luo, Yun-Fei, Li, You-Gui
Format: Artikel
Sprache:eng
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Zusammenfassung:An asymmetric dehydrogenative Diels-Alder reaction of 2-methyl-3-phenylmethylindoles and α,β-unsaturated aldehydes has been established. The successful in situ generation of the indole ortho-quinodimethane intermediate and the iminium activation of enals are the keys to success, providing various tetrahydrocarbazole derivatives with up to >99% ee.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b03251