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Exploring the scope of tandem palladium and isothiourea relay catalysis for the synthesis of α-amino acid derivatives

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Date
25/05/2020
Author
Bitai, Jacqueline
Slawin, Alexandra M. Z.
Cordes, David B.
Smith, Andrew D.
Keywords
Isothiourea
Palladium
Enantioselective catalysis
Amino acids
[2,3]-rearrangement
N-allylation
QD Chemistry
DAS
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Abstract
The scope and limitations of a tandem N-allylation/[2,3]-rearrangementprotocol are investigated through the incorporation of a variety of functionalgroups within an allylic phosphate precursor. This method uses readilyaccessible N,N-dimethylglycine aryl esters and functionalizedallylic phosphates, forming quaternary ammonium salts in situ in the presence of a palladium catalyst. Subsequentenantioselective [2,3]-sigmatropic rearrangement, promoted by the chiralisothiourea tetramisole, generates α-amino acid derivatives with two contiguousstereocenters. The incorporation of electron withdrawing ester and amide groupsgave the best results, furnishing the desired products in moderate to goodyields (29-70%), with low diastereocontrol (typically 60:40 dr) but highenantioselectivity (up to 90:10 er). These results indicate that substrate-catalystinteractions in the proposed transition state are sensitive to the substitutionpattern of the substrates.
Citation
Bitai , J , Slawin , A M Z , Cordes , D B & Smith , A D 2020 , ' Exploring the scope of tandem palladium and isothiourea relay catalysis for the synthesis of α-amino acid derivatives ' , Molecules , vol. 25 , no. 10 , 2463 . https://doi.org/10.3390/molecules25102463
Publication
Molecules
Status
Peer reviewed
DOI
https://doi.org/10.3390/molecules25102463
ISSN
1420-3049
Type
Journal article
Rights
Copyright © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
Description
Funding: This research was funded by the School of Chemistry, University of St Andrews. A.D.S. thanks the Royal Society for a Wolfson Research Merit Award.
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  • University of St Andrews Research
URI
http://hdl.handle.net/10023/20002

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