Isothiourea-catalyzed enantioselective synthesis of tetrahydro-α-carbolinones
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An isothiourea-catalyzed enantioselective annulation protocol using indolin-2-imines with a series of α,β-unsaturated p-nitrophenyl esters for the synthesis of tetrahydro-α-carbolinones was developed. Using 5 mol % of the isothiourea HyperBTM as the Lewis base catalyst, this process allows the enantioselective preparation of a range of C(4)-substituted tetrahydro-α-carbolinones in good to excellent yield and with high enantioselectivity (20 examples, 32–99% yield and up to 99:1 er).
Liu , H , Slawin , A M M & Smith , A D 2020 , ' Isothiourea-catalyzed enantioselective synthesis of tetrahydro-α-carbolinones ' , Organic Letters , vol. Articles ASAP . https://doi.org/10.1021/acs.orglett.9b04615
Copyright © 2020 American Chemical Society. This work has been made available online in accordance with publisher policies or with permission. Permission for further reuse of this content should be sought from the publisher or the rights holder. This is the author created accepted manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1021/acs.orglett.9b04615
DescriptionThe research leading to these results has received funding from the Royal Society (Newton Fellowship Programme, H. L.). A.D.S. thanks the Royal Society for a Wolfson Research Merit Award.
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