Synthesis 2018; 50(03): 607-616
DOI: 10.1055/s-0036-1590945
paper
© Georg Thieme Verlag Stuttgart · New York

Economical Synthesis of α-Amino Acids from a Novel Family of Easily Available Schiff Bases of Glycine Esters and 2-Hydroxy­benzophenone

Zalina T. Gugkaeva
A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, 119991 Moscow, Russian Federation   Email: yubel@ineos.ac.ru
,
A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, 119991 Moscow, Russian Federation   Email: yubel@ineos.ac.ru
Department of Inorganic Chemistry, People’s Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya Street, 117198 Moscow, Russian Federation
,
Margarita A. Moskalenko
A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, 119991 Moscow, Russian Federation   Email: yubel@ineos.ac.ru
,
Victor N. Khrustalev
Department of Inorganic Chemistry, People’s Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya Street, 117198 Moscow, Russian Federation
,
Yulia V. Nelyubina
A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, 119991 Moscow, Russian Federation   Email: yubel@ineos.ac.ru
,
Alexander S. Peregudov
A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, 119991 Moscow, Russian Federation   Email: yubel@ineos.ac.ru
,
Alan T. Tsaloev
Chemical Diversity Research Institute, 2a Rabochaya Street, 141400 Khimki, Moscow Region, Russian Federation
,
Victor I. Maleev
A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, 119991 Moscow, Russian Federation   Email: yubel@ineos.ac.ru
,
Yuri N. Belokon*
A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Street, 119991 Moscow, Russian Federation   Email: yubel@ineos.ac.ru
› Author Affiliations
This work was supported by the Russian Science Foundation (RSF grant 17-73-10016). X-ray studies were supported by the RUDN University Program 5-100.
Further Information

Publication History

Received: 07 September 2017

Accepted after revision: 07 October 2017

Publication Date:
09 November 2017 (eFirst)

Abstract

We report a novel, efficient, and easily prepared substrate/precursor family of Schiff bases of various glycine esters with 2-hydroxybenzophenone, and their use for the synthesis of amino acids in quantitative yields. The Michael addition of the substrates to methyl acrylate gave two different types of product (cyclic or chain), depending on the nature of the base. Also, we demonstrated that one of the new substrates could be involved in an asymmetric version of the alkylation reaction (70% ee).

Supporting Information

 
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