Synergistic Chemo/Biocatalytic Synthesis of Alkaloidal Tetrahydroquinolines

Sebastian C. Cosgrove; Shahed Hussain; Nicholas J. Turner; Stephen P. Marsden

doi:10.1021/acscatal.8b01220

Synergistic Chemo/Biocatalytic Synthesis of Alkaloidal Tetrahydroquinolines

Sebastian C. Cosgrove, Shahed Hussain, Nicholas J. Turner^*, Stephen P. Marsden

^*Corresponding author for this work

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

Abstract

The power of complementary chemocatalytic and biocatalytic transformations is demonstrated in the asymmetric synthesis of 2-substituted tetrahydroquinolines. A series of racemic tetrahydroquinolines were synthesized through a convergent one-pot Rh(I)-catalyzed addition/condensation sequence of alkyl vinyl ketones and aminophenylboronic acids. The resulting tetrahydroquinolines were thereafter shown to be substrates for the flavin-dependent enzyme cyclohexylamine oxidase, and preparative-scale deracemizations have been demonstrated on these high-value targets.

Original language	English
Pages (from-to)	5570-5573
Number of pages	4
Journal	ACS Catalysis
Volume	8
Issue number	6
Early online date	14 May 2018
DOIs	https://doi.org/10.1021/acscatal.8b01220
Publication status	Published - 1 Jun 2018

Keywords

alkaloidal tetrahydroquinoline
amine oxidase
biocatalysis
enzymatic deracemization
rhodium catalysis

Research Beacons, Institutes and Platforms

Manchester Institute of Biotechnology

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10.1021/acscatal.8b01220

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title = "Synergistic Chemo/Biocatalytic Synthesis of Alkaloidal Tetrahydroquinolines",

abstract = "The power of complementary chemocatalytic and biocatalytic transformations is demonstrated in the asymmetric synthesis of 2-substituted tetrahydroquinolines. A series of racemic tetrahydroquinolines were synthesized through a convergent one-pot Rh(I)-catalyzed addition/condensation sequence of alkyl vinyl ketones and aminophenylboronic acids. The resulting tetrahydroquinolines were thereafter shown to be substrates for the flavin-dependent enzyme cyclohexylamine oxidase, and preparative-scale deracemizations have been demonstrated on these high-value targets.",

keywords = "alkaloidal tetrahydroquinoline, amine oxidase, biocatalysis, enzymatic deracemization, rhodium catalysis",

author = "Cosgrove, \{Sebastian C.\} and Shahed Hussain and Turner, \{Nicholas J.\} and Marsden, \{Stephen P.\}",

year = "2018",

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doi = "10.1021/acscatal.8b01220",

language = "English",

volume = "8",

pages = "5570--5573",

journal = "ACS Catalysis",

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T1 - Synergistic Chemo/Biocatalytic Synthesis of Alkaloidal Tetrahydroquinolines

AU - Cosgrove, Sebastian C.

AU - Hussain, Shahed

AU - Turner, Nicholas J.

AU - Marsden, Stephen P.

PY - 2018/6/1

Y1 - 2018/6/1

N2 - The power of complementary chemocatalytic and biocatalytic transformations is demonstrated in the asymmetric synthesis of 2-substituted tetrahydroquinolines. A series of racemic tetrahydroquinolines were synthesized through a convergent one-pot Rh(I)-catalyzed addition/condensation sequence of alkyl vinyl ketones and aminophenylboronic acids. The resulting tetrahydroquinolines were thereafter shown to be substrates for the flavin-dependent enzyme cyclohexylamine oxidase, and preparative-scale deracemizations have been demonstrated on these high-value targets.

AB - The power of complementary chemocatalytic and biocatalytic transformations is demonstrated in the asymmetric synthesis of 2-substituted tetrahydroquinolines. A series of racemic tetrahydroquinolines were synthesized through a convergent one-pot Rh(I)-catalyzed addition/condensation sequence of alkyl vinyl ketones and aminophenylboronic acids. The resulting tetrahydroquinolines were thereafter shown to be substrates for the flavin-dependent enzyme cyclohexylamine oxidase, and preparative-scale deracemizations have been demonstrated on these high-value targets.

KW - alkaloidal tetrahydroquinoline

KW - amine oxidase

KW - biocatalysis

KW - enzymatic deracemization

KW - rhodium catalysis

UR - https://www.scopus.com/pages/publications/85047059637

U2 - 10.1021/acscatal.8b01220

DO - 10.1021/acscatal.8b01220

M3 - Article

AN - SCOPUS:85047059637

SN - 2155-5435

VL - 8

SP - 5570

EP - 5573

JO - ACS Catalysis

JF - ACS Catalysis

IS - 6

ER -

Synergistic Chemo/Biocatalytic Synthesis of Alkaloidal Tetrahydroquinolines

Abstract

Keywords

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