Enantioenriched α-substituted glutamates/pyroglutamates via enantioselective cyclopropenimine-catalyzed Michael addition of amino ester imines

A procedure for the enantioselective synthesis of α-substituted glutamates and pyroglutamates via a cyclopropenimine-catalyzed Michael addition of amino ester imines is described. Enantioselectivities of up to 94% have been achieved, and a variety of functional groups were found to be compatible. Th...

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Main Authors:	Zara M. Seibel, Jeffrey S. Bandar, Tristan H. Lambert
Format:	Article
Language:	English
Published:	Beilstein-Institut 2021-08-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	brønsted base cyclopropenimine enantioselective catalysis michael addition pyroglutamate
Online Access:	https://doi.org/10.3762/bjoc.17.134

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spelling	doaj-66cde01ece0945f6a732698c65862f072021-09-13T09:24:29ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972021-08-011712077208410.3762/bjoc.17.1341860-5397-17-134Enantioenriched α-substituted glutamates/pyroglutamates via enantioselective cyclopropenimine-catalyzed Michael addition of amino ester iminesZara M. Seibel0Jeffrey S. Bandar1Tristan H. Lambert2Department of Chemistry, Columbia University, New York, New York 10027, USADepartment of Chemistry, Columbia University, New York, New York 10027, USADepartment of Chemistry, Columbia University, New York, New York 10027, USAA procedure for the enantioselective synthesis of α-substituted glutamates and pyroglutamates via a cyclopropenimine-catalyzed Michael addition of amino ester imines is described. Enantioselectivities of up to 94% have been achieved, and a variety of functional groups were found to be compatible. The impact of the catalyst structure and imine substitution is discussed. Compared to other methods, this protocol allows for a broader and more enantioselective access to pyroglutamate derivatives.https://doi.org/10.3762/bjoc.17.134brønsted basecyclopropenimineenantioselective catalysismichael additionpyroglutamate
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Zara M. Seibel Jeffrey S. Bandar Tristan H. Lambert
spellingShingle	Zara M. Seibel Jeffrey S. Bandar Tristan H. Lambert Enantioenriched α-substituted glutamates/pyroglutamates via enantioselective cyclopropenimine-catalyzed Michael addition of amino ester imines Beilstein Journal of Organic Chemistry brønsted base cyclopropenimine enantioselective catalysis michael addition pyroglutamate
author_facet	Zara M. Seibel Jeffrey S. Bandar Tristan H. Lambert
author_sort	Zara M. Seibel
title	Enantioenriched α-substituted glutamates/pyroglutamates via enantioselective cyclopropenimine-catalyzed Michael addition of amino ester imines
title_short	Enantioenriched α-substituted glutamates/pyroglutamates via enantioselective cyclopropenimine-catalyzed Michael addition of amino ester imines
title_full	Enantioenriched α-substituted glutamates/pyroglutamates via enantioselective cyclopropenimine-catalyzed Michael addition of amino ester imines
title_fullStr	Enantioenriched α-substituted glutamates/pyroglutamates via enantioselective cyclopropenimine-catalyzed Michael addition of amino ester imines
title_full_unstemmed	Enantioenriched α-substituted glutamates/pyroglutamates via enantioselective cyclopropenimine-catalyzed Michael addition of amino ester imines
title_sort	enantioenriched α-substituted glutamates/pyroglutamates via enantioselective cyclopropenimine-catalyzed michael addition of amino ester imines
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2021-08-01
description	A procedure for the enantioselective synthesis of α-substituted glutamates and pyroglutamates via a cyclopropenimine-catalyzed Michael addition of amino ester imines is described. Enantioselectivities of up to 94% have been achieved, and a variety of functional groups were found to be compatible. The impact of the catalyst structure and imine substitution is discussed. Compared to other methods, this protocol allows for a broader and more enantioselective access to pyroglutamate derivatives.
topic	brønsted base cyclopropenimine enantioselective catalysis michael addition pyroglutamate
url	https://doi.org/10.3762/bjoc.17.134
work_keys_str_mv	AT zaramseibel enantioenrichedasubstitutedglutamatespyroglutamatesviaenantioselectivecyclopropeniminecatalyzedmichaeladditionofaminoesterimines AT jeffreysbandar enantioenrichedasubstitutedglutamatespyroglutamatesviaenantioselectivecyclopropeniminecatalyzedmichaeladditionofaminoesterimines AT tristanhlambert enantioenrichedasubstitutedglutamatespyroglutamatesviaenantioselectivecyclopropeniminecatalyzedmichaeladditionofaminoesterimines
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Enantioenriched α-substituted glutamates/pyroglutamates via enantioselective cyclopropenimine-catalyzed Michael addition of amino ester imines

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