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

14 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

Bibliographical note

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

Keywords

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

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1002/ejoc.201801305

Cite this

@article{94c17cc498474ebe89cabee94b6b9cd9,

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

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",

author = "Antonin Mambrini and Didier Gori and Cyrille Kouklovsky and Heejin Kim and Yoshida, {Jun ichi} and Val{\'e}rie Alezra",

note = "Funding Information: This research was supported by the Minist{\`e}re de l′Enseigne-ment Sup{\'e}rieur, de la Recherche et de l'Innovation (doctoral grant to A. M.). Publisher Copyright: {\textcopyright} 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2018",

month = dec,

day = "19",

doi = "10.1002/ejoc.201801305",

language = "English",

volume = "2018",

pages = "6754--6757",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

number = "47",

}

TY - JOUR

T1 - Memory of Chirality in a Flow-Based System

T2 - Enantioselective Synthesis of Quaternary α-Amino Acids Using Flow Microreactors

AU - Mambrini, Antonin

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

PY - 2018/12/19

Y1 - 2018/12/19

N2 - 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.

AB - 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.

KW - Amino acids

KW - Asymmetric synthesis

KW - Continuous flow

KW - Flash chemistry

KW - Flow chemistry

KW - Memory of chirality

UR - http://www.scopus.com/inward/record.url?scp=85056132558&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201801305

DO - 10.1002/ejoc.201801305

M3 - Article

AN - SCOPUS:85056132558

SN - 1434-193X

VL - 2018

SP - 6754

EP - 6757

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 47

ER -

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

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this