Memory of Chirality in a Flow-Based System: Enantioselective Synthesis of Quaternary α-Amino Acids Using Flow Microreactors

Antonin Mambrini; Didier Gori; Cyrille Kouklovsky; Heejin Kim; Jun ichi Yoshida; Valérie Alezra

doi:10.1002/ejoc.201801305

Memory of Chirality in a Flow-Based System: Enantioselective Synthesis of Quaternary α-Amino Acids Using Flow Microreactors

Antonin Mambrini, Didier Gori, Cyrille Kouklovsky, Heejin Kim, Jun ichi Yoshida, Valérie Alezra

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

13 Citations (Scopus)

Abstract

Enantioselective synthesis of quaternary α-amino acids based on alkylation of a conformationally unstable enolate according to a memory-of-chirality strategy was successfully adapted to a flow-based system. This allows for the scale-up of this enantioselective process with reaction residence times of less than three minutes. The enantiomeric excess values are similar to those obtained in the batch process.

Original language	English
Pages (from-to)	6754-6757
Number of pages	4
Journal	European Journal of Organic Chemistry
Volume	2018
Issue number	47
DOIs	https://doi.org/10.1002/ejoc.201801305
Publication status	Published - 2018 Dec 19
Externally published	Yes

Keywords

Amino acids
Asymmetric synthesis
Continuous flow
Flash chemistry
Flow chemistry
Memory of chirality

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.201801305

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abstract = "Enantioselective synthesis of quaternary α-amino acids based on alkylation of a conformationally unstable enolate according to a memory-of-chirality strategy was successfully adapted to a flow-based system. This allows for the scale-up of this enantioselective process with reaction residence times of less than three minutes. The enantiomeric excess values are similar to those obtained in the batch process.",

keywords = "Amino acids, Asymmetric synthesis, Continuous flow, Flash chemistry, Flow chemistry, Memory of chirality",

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AU - Gori, Didier

AU - Kouklovsky, Cyrille

AU - Kim, Heejin

AU - Yoshida, Jun ichi

AU - Alezra, Valérie

N1 - Funding Information: This research was supported by the Ministère de l′Enseigne-ment Supérieur, de la Recherche et de l'Innovation (doctoral grant to A. M.). Publisher Copyright: © 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

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KW - Flash chemistry

KW - Flow chemistry

KW - Memory of chirality

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Memory of Chirality in a Flow-Based System: Enantioselective Synthesis of Quaternary α-Amino Acids Using Flow Microreactors

Abstract

Keywords

ASJC Scopus subject areas

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