Alkylative Amination of Biogenic Furans through Imine-to-Azaallyl Anion Umpolung

Fabian Blume; Mhd Haitham Albeiruty; Jan Deska

doi:10.1055/s-0034-1380201

Alkylative Amination of Biogenic Furans through Imine-to-Azaallyl Anion Umpolung

Fabian Blume^*, Mhd Haitham Albeiruty, Jan Deska

^*Corresponding author for this work

Not published at Aalto University

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

9 Citations (Scopus)

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Abstract

Starting from biogenic furfurals, an operationally simple and scalable condensation-umpolung-alkylation protocol was employed in the synthesis of racemic furfurylamines. Subsequent enzymatic kinetic resolution by -transaminase or lipase biocatalysts allows for the preparation of functionalized heterocyclic building blocks from biogenic base chemicals in optically pure form.

Original language	English
Pages (from-to)	2093-2099
Number of pages	7
Journal	SYNTHESIS: STUTTGART
Volume	47
Issue number	14
DOIs	https://doi.org/10.1055/s-0034-1380201
Publication status	Published - Jul 2015
MoE publication type	A1 Journal article-refereed

Keywords

furfural
amines
umpolung
biocatalysis
transaminase
ASYMMETRIC-SYNTHESIS
BUILDING-BLOCKS
REARRANGEMENT
ARYLATION
BOND

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10.1055/s-0034-1380201

CHEM_Blume_et_el_Alkylative_amination_of_2018_SynthesisAccepted author manuscript, 383 KBLicence: Unspecified

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title = "Alkylative Amination of Biogenic Furans through Imine-to-Azaallyl Anion Umpolung",

abstract = "Starting from biogenic furfurals, an operationally simple and scalable condensation-umpolung-alkylation protocol was employed in the synthesis of racemic furfurylamines. Subsequent enzymatic kinetic resolution by -transaminase or lipase biocatalysts allows for the preparation of functionalized heterocyclic building blocks from biogenic base chemicals in optically pure form.",

keywords = "furfural, amines, umpolung, biocatalysis, transaminase, ASYMMETRIC-SYNTHESIS, BUILDING-BLOCKS, REARRANGEMENT, ARYLATION, BOND",

author = "Fabian Blume and Albeiruty, {Mhd Haitham} and Jan Deska",

year = "2015",

month = jul,

doi = "10.1055/s-0034-1380201",

language = "English",

volume = "47",

pages = "2093--2099",

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T1 - Alkylative Amination of Biogenic Furans through Imine-to-Azaallyl Anion Umpolung

AU - Blume, Fabian

AU - Albeiruty, Mhd Haitham

AU - Deska, Jan

PY - 2015/7

Y1 - 2015/7

N2 - Starting from biogenic furfurals, an operationally simple and scalable condensation-umpolung-alkylation protocol was employed in the synthesis of racemic furfurylamines. Subsequent enzymatic kinetic resolution by -transaminase or lipase biocatalysts allows for the preparation of functionalized heterocyclic building blocks from biogenic base chemicals in optically pure form.

AB - Starting from biogenic furfurals, an operationally simple and scalable condensation-umpolung-alkylation protocol was employed in the synthesis of racemic furfurylamines. Subsequent enzymatic kinetic resolution by -transaminase or lipase biocatalysts allows for the preparation of functionalized heterocyclic building blocks from biogenic base chemicals in optically pure form.

KW - furfural

KW - amines

KW - umpolung

KW - biocatalysis

KW - transaminase

KW - ASYMMETRIC-SYNTHESIS

KW - BUILDING-BLOCKS

KW - REARRANGEMENT

KW - ARYLATION

KW - BOND

U2 - 10.1055/s-0034-1380201

DO - 10.1055/s-0034-1380201

M3 - Article

VL - 47

SP - 2093

EP - 2099

JO - SYNTHESIS: STUTTGART

JF - SYNTHESIS: STUTTGART

SN - 0039-7881

IS - 14

ER -

Alkylative Amination of Biogenic Furans through Imine-to-Azaallyl Anion Umpolung

Abstract

Keywords

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