(S)-(−)-Fluorenylethylchloroformate (FLEC); preparation using asymmetric transfer hydrogenation and application to the analysis and resolution of amines

Mohammad Al Amin; Michelle A. Camerino; Simon J. Mountford; Xiao Ma; David T. Manallack; David K. Chalmers; Martin Wills; Philip E. Thompson

doi:10.1016/j.tet.2019.130591

(S)-(−)-Fluorenylethylchloroformate (FLEC); preparation using asymmetric transfer hydrogenation and application to the analysis and resolution of amines

Mohammad Al Amin, Michelle A. Camerino, Simon J. Mountford, Xiao Ma, David T. Manallack, David K. Chalmers, Martin Wills, Philip E. Thompson

Medicinal Chemistry

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

4 Citations (Scopus)

Abstract

Fluorenylethylchoroformate (FLEC) is a valuable chiral derivatisation reagent that is used for the resolution of a wide variety of chiral amines. Herein, we describe an improved preparation of (S)-(−)-FLEC using an efficient asymmetric catalytic transfer hydrogenation as the key step. We also demonstrate the application of FLEC as a chiral Fmoc equivalent for chiral resolution, with facile deprotection, of tetrahydroquinaldines, and its capacity for inducing regioselective outcomes in nitration reactions.

Original language	English
Article number	130591
Pages (from-to)	1-7
Number of pages	7
Journal	Tetrahedron
Volume	75
Issue number	43
DOIs	https://doi.org/10.1016/j.tet.2019.130591
Publication status	Published - 1 Jan 2019

Keywords

1-(9H-Fluoren-9-yl)ethan-1-ol
Asymmetric transfer hydrogenation
Chiral derivatisation
Chiral Fmoc
Chiral resolution
Fluorenylethylchoroformate

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10.1016/j.tet.2019.130591

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title = "(S)-(−)-Fluorenylethylchloroformate (FLEC); preparation using asymmetric transfer hydrogenation and application to the analysis and resolution of amines",

abstract = "Fluorenylethylchoroformate (FLEC) is a valuable chiral derivatisation reagent that is used for the resolution of a wide variety of chiral amines. Herein, we describe an improved preparation of (S)-(−)-FLEC using an efficient asymmetric catalytic transfer hydrogenation as the key step. We also demonstrate the application of FLEC as a chiral Fmoc equivalent for chiral resolution, with facile deprotection, of tetrahydroquinaldines, and its capacity for inducing regioselective outcomes in nitration reactions.",

keywords = "1-(9H-Fluoren-9-yl)ethan-1-ol, Asymmetric transfer hydrogenation, Chiral derivatisation, Chiral Fmoc, Chiral resolution, Fluorenylethylchoroformate",

author = "{Al Amin}, Mohammad and Camerino, {Michelle A.} and Mountford, {Simon J.} and Xiao Ma and Manallack, {David T.} and Chalmers, {David K.} and Martin Wills and Thompson, {Philip E.}",

year = "2019",

month = jan,

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doi = "10.1016/j.tet.2019.130591",

language = "English",

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journal = "Tetrahedron",

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TY - JOUR

T1 - (S)-(−)-Fluorenylethylchloroformate (FLEC); preparation using asymmetric transfer hydrogenation and application to the analysis and resolution of amines

AU - Al Amin, Mohammad

AU - Camerino, Michelle A.

AU - Mountford, Simon J.

AU - Ma, Xiao

AU - Manallack, David T.

AU - Chalmers, David K.

AU - Wills, Martin

AU - Thompson, Philip E.

PY - 2019/1/1

Y1 - 2019/1/1

N2 - Fluorenylethylchoroformate (FLEC) is a valuable chiral derivatisation reagent that is used for the resolution of a wide variety of chiral amines. Herein, we describe an improved preparation of (S)-(−)-FLEC using an efficient asymmetric catalytic transfer hydrogenation as the key step. We also demonstrate the application of FLEC as a chiral Fmoc equivalent for chiral resolution, with facile deprotection, of tetrahydroquinaldines, and its capacity for inducing regioselective outcomes in nitration reactions.

AB - Fluorenylethylchoroformate (FLEC) is a valuable chiral derivatisation reagent that is used for the resolution of a wide variety of chiral amines. Herein, we describe an improved preparation of (S)-(−)-FLEC using an efficient asymmetric catalytic transfer hydrogenation as the key step. We also demonstrate the application of FLEC as a chiral Fmoc equivalent for chiral resolution, with facile deprotection, of tetrahydroquinaldines, and its capacity for inducing regioselective outcomes in nitration reactions.

KW - 1-(9H-Fluoren-9-yl)ethan-1-ol

KW - Asymmetric transfer hydrogenation

KW - Chiral derivatisation

KW - Chiral Fmoc

KW - Chiral resolution

KW - Fluorenylethylchoroformate

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U2 - 10.1016/j.tet.2019.130591

DO - 10.1016/j.tet.2019.130591

M3 - Article

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SN - 0040-4020

VL - 75

SP - 1

EP - 7

JO - Tetrahedron

JF - Tetrahedron

IS - 43

M1 - 130591

ER -

(S)-(−)-Fluorenylethylchloroformate (FLEC); preparation using asymmetric transfer hydrogenation and application to the analysis and resolution of amines

Abstract

Keywords

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