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Chromium-Catalyzed Asymmetric Dearomatization–Addition Reactions of Halomethyloxazoles and Indoles

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The asymmetric dearomatization–addition reaction of halo­methyloxazoles and halomethylindoles with aldehydes is realized in the presence of a carbazole-based bisoxazoline CrCl2 complex to afford the corresponding enantioenriched, hydroxylated oxazoline and indoline… Click to show full abstract

The asymmetric dearomatization–addition reaction of halo­methyloxazoles and halomethylindoles with aldehydes is realized in the presence of a carbazole-based bisoxazoline CrCl2 complex to afford the corresponding enantioenriched, hydroxylated oxazoline and indoline products. The observed excellent chemo-, regio-, diastereo- and enantioselectivities are notable advantages of this protocol. The strategy established in this study is expected to find application in the synthesis of azaheterocycles with biological significance and useful functionalities.

Keywords: asymmetric dearomatization; chromium catalyzed; dearomatization addition; catalyzed asymmetric

Journal Title: Synthesis
Year Published: 2018

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