Isothiourea-catalyzed enantioselective functionalisation of glycine Schiff base aryl esters via 1,6- and 1,4-additions

Lotte Stockhammer; Rebecca Craik; Uwe Monkowius; David B. Cordes; Andrew D. Smith; Mario Waser

doi:10.1002/ceur.202300015

Isothiourea-catalyzed enantioselective functionalisation of glycine Schiff base aryl esters via 1,6- and 1,4-additions

Lotte Stockhammer, Rebecca Craik, Uwe Monkowius, David B. Cordes, Andrew D. Smith^*, Mario Waser

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

Abstract

The enantioselective α-functionalisation of glycine Schiff base aryl esters through isothiourea catalysis is successfully demonstrated for 1,6-additions to para-quinone methides (21 examples, up to 95 : 5 dr and 96 : 4 er) and 1,4- additions to methylene substituted dicarbonyl or disulfonyl Michael acceptors (17 examples, up to 98 : 2 er). This nucleophilic organocatalysis approach gives access to a range of α-functionalised α-amino acid derivatives and further transformations of the activated aryl ester group provide a straightforward entry to advanced amino acid-based esters, amides or thioesters.

Original language	English
Article number	e202300015
Number of pages	9
Journal	Chemistry Europe
Volume	1
Issue number	1
Early online date	3 May 2023
DOIs	https://doi.org/10.1002/ceur.202300015
Publication status	Published - 3 Jul 2023

Keywords

Isothiourea
α-amino acid derivatives
Glycine Schiff base
Enantioselective
1,6- and 1,4-addition

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10.1002/ceur.202300015Licence: CC BY

Stockhammer _2023_CE_Isothiourea‐Catalyzed_CC
Copyright © 2023 The Authors. ChemistryEurope published by Chemistry Europe and Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
Final published version, 11.5 MBLicence: CC BY

CRITICAT CDT: Critical Resource Catalysis - CRITICAT
Smith, A. D. (PI), Nolan, S. P. (CoI) & Westwood, N. J. (CoI)
EPSRC
1/05/14 → 31/10/22
Project: Standard

data underpinning "Isothiourea-Catalyzed Enantioselective Functionalisation of Glycine Schiff Base Aryl Esters via 1,6- and 1,4-additions"
Smith, A. D. (Creator), Craik, R. (Owner), Cordes, D. B. (Contributor), Stockhammer, L. (Creator), Monkowius, U. (Creator) & Waser, M. (Creator), University of St Andrews, 24 May 2023
DOI: 10.17630/631a7545-ad96-427c-aa3f-a18664e93537
Dataset

File

Cite this

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title = "Isothiourea-catalyzed enantioselective functionalisation of glycine Schiff base aryl esters via 1,6- and 1,4-additions",

abstract = "The enantioselective α-functionalisation of glycine Schiff base aryl esters through isothiourea catalysis is successfully demonstrated for 1,6-additions to para-quinone methides (21 examples, up to 95 : 5 dr and 96 : 4 er) and 1,4- additions to methylene substituted dicarbonyl or disulfonyl Michael acceptors (17 examples, up to 98 : 2 er). This nucleophilic organocatalysis approach gives access to a range of α-functionalised α-amino acid derivatives and further transformations of the activated aryl ester group provide a straightforward entry to advanced amino acid-based esters, amides or thioesters.",

keywords = "Isothiourea, α-amino acid derivatives, Glycine Schiff base, Enantioselective, 1,6- and 1,4-addition",

author = "Lotte Stockhammer and Rebecca Craik and Uwe Monkowius and Cordes, {David B.} and Smith, {Andrew D.} and Mario Waser",

note = "The St Andrews team thanks the EPSRC Centre for Doctoral Training in Critical Resource Catalysis (CRITICAT, grant code EP/L016419/1) (RC) for funding. The Linz team gratefully acknowledges generous financial support by the Austrian Science Funds (FWF) through project No. P31784. ",

year = "2023",

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doi = "10.1002/ceur.202300015",

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T1 - Isothiourea-catalyzed enantioselective functionalisation of glycine Schiff base aryl esters via 1,6- and 1,4-additions

AU - Stockhammer, Lotte

AU - Craik, Rebecca

AU - Monkowius, Uwe

AU - Cordes, David B.

AU - Smith, Andrew D.

AU - Waser, Mario

N1 - The St Andrews team thanks the EPSRC Centre for Doctoral Training in Critical Resource Catalysis (CRITICAT, grant code EP/L016419/1) (RC) for funding. The Linz team gratefully acknowledges generous financial support by the Austrian Science Funds (FWF) through project No. P31784.

PY - 2023/7/3

Y1 - 2023/7/3

N2 - The enantioselective α-functionalisation of glycine Schiff base aryl esters through isothiourea catalysis is successfully demonstrated for 1,6-additions to para-quinone methides (21 examples, up to 95 : 5 dr and 96 : 4 er) and 1,4- additions to methylene substituted dicarbonyl or disulfonyl Michael acceptors (17 examples, up to 98 : 2 er). This nucleophilic organocatalysis approach gives access to a range of α-functionalised α-amino acid derivatives and further transformations of the activated aryl ester group provide a straightforward entry to advanced amino acid-based esters, amides or thioesters.

AB - The enantioselective α-functionalisation of glycine Schiff base aryl esters through isothiourea catalysis is successfully demonstrated for 1,6-additions to para-quinone methides (21 examples, up to 95 : 5 dr and 96 : 4 er) and 1,4- additions to methylene substituted dicarbonyl or disulfonyl Michael acceptors (17 examples, up to 98 : 2 er). This nucleophilic organocatalysis approach gives access to a range of α-functionalised α-amino acid derivatives and further transformations of the activated aryl ester group provide a straightforward entry to advanced amino acid-based esters, amides or thioesters.

KW - Isothiourea

KW - α-amino acid derivatives

KW - Glycine Schiff base

KW - Enantioselective

KW - 1,6- and 1,4-addition

U2 - 10.1002/ceur.202300015

DO - 10.1002/ceur.202300015

M3 - Article

SN - 2751-4765

VL - 1

JO - Chemistry Europe

JF - Chemistry Europe

IS - 1

M1 - e202300015

ER -

Isothiourea-catalyzed enantioselective functionalisation of glycine Schiff base aryl esters via 1,6- and 1,4-additions

Abstract

Keywords

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data underpinning "Isothiourea-Catalyzed Enantioselective Functionalisation of Glycine Schiff Base Aryl Esters via 1,6- and 1,4-additions"

Cite this