Enzymatic Kinetic Resolution of 2-Piperidineethanol for the Enantioselective Targeted and Diversity Oriented Synthesis

2-Piperidineethanol (1) and its corresponding N-protected aldehyde (2) were used for the synthesis of several natural and synthetic compounds. The existence of a stereocenter at position 2 of the piperidine skeleton and the presence of an easily-functionalized group, such as the alcohol, set 1 as a...

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Main Authors: Dario Perdicchia, Michael S. Christodoulou, Gaia Fumagalli, Francesco Calogero, Cristina Marucci, Daniele Passarella
Format: Article
Language:English
Published: MDPI AG 2015-12-01
Series:International Journal of Molecular Sciences
Subjects:
Online Access:http://www.mdpi.com/1422-0067/17/1/17
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spelling doaj-13f3e8811c0148e4aded313aea9467832020-11-24T23:26:37ZengMDPI AGInternational Journal of Molecular Sciences1422-00672015-12-011711710.3390/ijms17010017ijms17010017Enzymatic Kinetic Resolution of 2-Piperidineethanol for the Enantioselective Targeted and Diversity Oriented SynthesisDario Perdicchia0Michael S. Christodoulou1Gaia Fumagalli2Francesco Calogero3Cristina Marucci4Daniele Passarella5Dipartimento di Chimica, Universita degli Studi di Milano, Via Golgi 19, 20133 Milano, ItalyDipartimento di Chimica, Universita degli Studi di Milano, Via Golgi 19, 20133 Milano, ItalyDipartimento di Chimica, Universita degli Studi di Milano, Via Golgi 19, 20133 Milano, ItalyDipartimento di Chimica, Universita degli Studi di Milano, Via Golgi 19, 20133 Milano, ItalyDipartimento di Chimica, Universita degli Studi di Milano, Via Golgi 19, 20133 Milano, ItalyDipartimento di Chimica, Universita degli Studi di Milano, Via Golgi 19, 20133 Milano, Italy2-Piperidineethanol (1) and its corresponding N-protected aldehyde (2) were used for the synthesis of several natural and synthetic compounds. The existence of a stereocenter at position 2 of the piperidine skeleton and the presence of an easily-functionalized group, such as the alcohol, set 1 as a valuable starting material for enantioselective synthesis. Herein, are presented both synthetic and enzymatic methods for the resolution of the racemic 1, as well as an overview of synthesized natural products starting from the enantiopure 1.http://www.mdpi.com/1422-0067/17/1/172-piperidineethanolpiperidine alkaloidsenzymatic resolutionalkaloid synthesis
collection DOAJ
language English
format Article
sources DOAJ
author Dario Perdicchia
Michael S. Christodoulou
Gaia Fumagalli
Francesco Calogero
Cristina Marucci
Daniele Passarella
spellingShingle Dario Perdicchia
Michael S. Christodoulou
Gaia Fumagalli
Francesco Calogero
Cristina Marucci
Daniele Passarella
Enzymatic Kinetic Resolution of 2-Piperidineethanol for the Enantioselective Targeted and Diversity Oriented Synthesis
International Journal of Molecular Sciences
2-piperidineethanol
piperidine alkaloids
enzymatic resolution
alkaloid synthesis
author_facet Dario Perdicchia
Michael S. Christodoulou
Gaia Fumagalli
Francesco Calogero
Cristina Marucci
Daniele Passarella
author_sort Dario Perdicchia
title Enzymatic Kinetic Resolution of 2-Piperidineethanol for the Enantioselective Targeted and Diversity Oriented Synthesis
title_short Enzymatic Kinetic Resolution of 2-Piperidineethanol for the Enantioselective Targeted and Diversity Oriented Synthesis
title_full Enzymatic Kinetic Resolution of 2-Piperidineethanol for the Enantioselective Targeted and Diversity Oriented Synthesis
title_fullStr Enzymatic Kinetic Resolution of 2-Piperidineethanol for the Enantioselective Targeted and Diversity Oriented Synthesis
title_full_unstemmed Enzymatic Kinetic Resolution of 2-Piperidineethanol for the Enantioselective Targeted and Diversity Oriented Synthesis
title_sort enzymatic kinetic resolution of 2-piperidineethanol for the enantioselective targeted and diversity oriented synthesis
publisher MDPI AG
series International Journal of Molecular Sciences
issn 1422-0067
publishDate 2015-12-01
description 2-Piperidineethanol (1) and its corresponding N-protected aldehyde (2) were used for the synthesis of several natural and synthetic compounds. The existence of a stereocenter at position 2 of the piperidine skeleton and the presence of an easily-functionalized group, such as the alcohol, set 1 as a valuable starting material for enantioselective synthesis. Herein, are presented both synthetic and enzymatic methods for the resolution of the racemic 1, as well as an overview of synthesized natural products starting from the enantiopure 1.
topic 2-piperidineethanol
piperidine alkaloids
enzymatic resolution
alkaloid synthesis
url http://www.mdpi.com/1422-0067/17/1/17
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