Isothiourea-catalyzed enantioselective synthesis of tetrahydro-α-carbolinones

Honglei Liu, Alexandra M. M. Slawin, Andrew D. Smith*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)
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Abstract


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).
Original languageEnglish
JournalOrganic Letters
VolumeArticles ASAP
Early online date6 Feb 2020
DOIs
Publication statusE-pub ahead of print - 6 Feb 2020

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