Towards a universal organocatalyst for the synthesis of enantioenriched phenylalanine derivatives by enantioselective decarboxylative protonation
Towards a universal organocatalyst for the synthesis of enantioenriched phenylalanine derivatives by enantioselective decarboxylative protonation
Access to enantioenriched non-proteogenic phenylalanine derivatives is described using the enantioselective decarboxylative protonation reaction of amidohemimalonate esters catalysed by various cinchona-based compounds. This study compares the catalytic efficiency as well as the enantioselectivity induced by three types of common organocatalysts, namely thioureas, squaramides and bis-cinchona squaramides. One of the main outcome of this work is the observation of a significant influence of the N-protecting group of the hemimalonate on its interaction with the catalyst. This methodology carried out under mild conditions exhibits good substrate scope and functional group tolerance. A substoichiometric amount of catalyst can also be used in certain cases while affording good yields and selectivities.
4599-4603
Pigeaux, Morgane
979cb015-77ba-49cd-82ba-c2186c811016
Laporte, Romain
b05284ef-d24c-4e44-bb2f-385c68e9a672
Harrowven, David
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Baudoux, Jérôme
b2ac6a6e-2cbc-49d4-820e-628745f48456
Rouden, Jacques
fc34b268-018c-4095-8048-e0557acac98c
12 October 2016
Pigeaux, Morgane
979cb015-77ba-49cd-82ba-c2186c811016
Laporte, Romain
b05284ef-d24c-4e44-bb2f-385c68e9a672
Harrowven, David
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Baudoux, Jérôme
b2ac6a6e-2cbc-49d4-820e-628745f48456
Rouden, Jacques
fc34b268-018c-4095-8048-e0557acac98c
Pigeaux, Morgane, Laporte, Romain, Harrowven, David, Baudoux, Jérôme and Rouden, Jacques
(2016)
Towards a universal organocatalyst for the synthesis of enantioenriched phenylalanine derivatives by enantioselective decarboxylative protonation.
Tetrahedron Letters, 57 (41), .
(doi:10.1016/j.tetlet.2016.09.001).
Abstract
Access to enantioenriched non-proteogenic phenylalanine derivatives is described using the enantioselective decarboxylative protonation reaction of amidohemimalonate esters catalysed by various cinchona-based compounds. This study compares the catalytic efficiency as well as the enantioselectivity induced by three types of common organocatalysts, namely thioureas, squaramides and bis-cinchona squaramides. One of the main outcome of this work is the observation of a significant influence of the N-protecting group of the hemimalonate on its interaction with the catalyst. This methodology carried out under mild conditions exhibits good substrate scope and functional group tolerance. A substoichiometric amount of catalyst can also be used in certain cases while affording good yields and selectivities.
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Accepted/In Press date: 1 September 2016
e-pub ahead of print date: 2 September 2016
Published date: 12 October 2016
Organisations:
Organic Chemistry: Synthesis, Catalysis and Flow
Identifiers
Local EPrints ID: 402399
URI: http://eprints.soton.ac.uk/id/eprint/402399
ISSN: 0040-4039
PURE UUID: 3125427f-5b62-46cd-bf05-12ad7bfb4d1b
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Date deposited: 08 Nov 2016 11:58
Last modified: 16 Mar 2024 02:46
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Contributors
Author:
Morgane Pigeaux
Author:
Romain Laporte
Author:
Jérôme Baudoux
Author:
Jacques Rouden
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