Isothiourea-catalyzed enantioselective synthesis of tetrahydro-α-carbolinones

Honglei Liu; Alexandra M. M. Slawin; Andrew D. Smith

doi:10.1021/acs.orglett.9b04615

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 journal › Article › peer-review

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 language	English
Journal	Organic Letters
Volume	Articles ASAP
Early online date	6 Feb 2020
DOIs	https://doi.org/10.1021/acs.orglett.9b04615
Publication status	E-pub ahead of print - 6 Feb 2020

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Liu_2020_OL_AAM
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
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Honglei Liu - Newton Fellowship: Dynamic Kinetic Resolution/Desynnetrisation of Atropisomeric Biaryl Diols Using Isothioureas
Smith, A. D. (PI)
The Royal Society
1/02/18 → 31/01/20
Project: Fellowship
RS Wolfson Merit Award: Developing Catalysis Research: New Reaction Discoveries and Practical Applications
Smith, A. D. (PI)
The Royal Society
1/01/15 → 31/12/19
Project: Fellowship

Data undepinning "Isothiourea-Catalyzed Enantioselective Synthesis of Tetrahydro-α-carbolinones"
Smith, A. D. (Creator) & Liu, H. (Creator), University of St Andrews, 2019
DOI: 10.17630/46afe239-6329-434e-b590-f53fe3f7de66
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title = "Isothiourea-catalyzed enantioselective synthesis of tetrahydro-α-carbolinones",

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).",

author = "Honglei Liu and Slawin, {Alexandra M. M.} and Smith, {Andrew D.}",

note = "The 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. ",

year = "2020",

month = feb,

day = "6",

doi = "10.1021/acs.orglett.9b04615",

language = "English",

volume = "Articles ASAP",

journal = "Organic Letters",

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TY - JOUR

T1 - Isothiourea-catalyzed enantioselective synthesis of tetrahydro-α-carbolinones

AU - Liu, Honglei

AU - Slawin, Alexandra M. M.

AU - Smith, Andrew D.

N1 - The 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.

PY - 2020/2/6

Y1 - 2020/2/6

N2 - 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).

AB - 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).

U2 - 10.1021/acs.orglett.9b04615

DO - 10.1021/acs.orglett.9b04615

M3 - Article

SN - 1523-7060

VL - Articles ASAP

JO - Organic Letters

JF - Organic Letters

ER -

Isothiourea-catalyzed enantioselective synthesis of tetrahydro-α-carbolinones

Abstract

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Projects

Honglei Liu - Newton Fellowship: Dynamic Kinetic Resolution/Desynnetrisation of Atropisomeric Biaryl Diols Using Isothioureas

RS Wolfson Merit Award: Developing Catalysis Research: New Reaction Discoveries and Practical Applications

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Data undepinning "Isothiourea-Catalyzed Enantioselective Synthesis of Tetrahydro-α-carbolinones"

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