Synergistic Catalysis: Highly Enantioselective Acetyl Aza-arene Addition to Enals

Marta Meazza; Gabriela Sitinova; Cecilia Poderi; Michele Mancinelli; Kaiheng Zhang; Andrea Mazzanti; Ramon Rios Torres

doi:10.1002/chem.201802303

Synergistic Catalysis: Highly Enantioselective Acetyl Aza-arene Addition to Enals

Marta Meazza
, Gabriela Sitinova
, Cecilia Poderi
, Michele Mancinelli
, Kaiheng Zhang
, Andrea Mazzanti
, Ramon Rios Torres

Chemistry

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

16 Scopus citations

Abstract

A novel catalytic enantioselective methodology based on synergistic catalysis for the synthesis of chiral 2-acyl pyridines and pyrazines is reported. The strategy involves the metal–Lewis acid activation of acetyl aza-arenes and the secondary-amine activation of enals. The proposed mechanism is supported by DFT calculations.

Original language	British English
Pages (from-to)	13306-13310
Number of pages	5
Journal	Chemistry - A European Journal
Volume	24
Issue number	50
DOIs	https://doi.org/10.1002/chem.201802303
State	Published - 6 Sep 2018

Keywords

acetyl aza-arenes
enals
Michael addition
secondary amine catalysis
synergistic catalysis

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title = "Synergistic Catalysis: Highly Enantioselective Acetyl Aza-arene Addition to Enals",

abstract = "A novel catalytic enantioselective methodology based on synergistic catalysis for the synthesis of chiral 2-acyl pyridines and pyrazines is reported. The strategy involves the metal–Lewis acid activation of acetyl aza-arenes and the secondary-amine activation of enals. The proposed mechanism is supported by DFT calculations.",

keywords = "acetyl aza-arenes, enals, Michael addition, secondary amine catalysis, synergistic catalysis",

author = "Marta Meazza and Gabriela Sitinova and Cecilia Poderi and Michele Mancinelli and Kaiheng Zhang and Andrea Mazzanti and Torres, \{Ramon Rios\}",

note = "Funding Information: Abstract: A novel catalytic enantioselective methodology based on synergistic catalysis for the synthesis of chiral 2-acyl pyridines and pyrazines is reported. The strategy in- volves the metal–Lewis acid activation of acetyl aza-arenes and the secondary-amine activation of enals. The proposed mechanism is supported by DFT calculations. Funding Information: M.M. and R.R are grateful for EPSRC Core Capability Funding (EP/K039466/1). Financial contribution was received by A.M., M.M., and C.P. from the University of Bologna (RFO funds 2015 and 2016). Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

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doi = "10.1002/chem.201802303",

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T2 - Highly Enantioselective Acetyl Aza-arene Addition to Enals

AU - Meazza, Marta

AU - Sitinova, Gabriela

AU - Poderi, Cecilia

AU - Mancinelli, Michele

AU - Zhang, Kaiheng

AU - Mazzanti, Andrea

AU - Torres, Ramon Rios

N1 - Funding Information: Abstract: A novel catalytic enantioselective methodology based on synergistic catalysis for the synthesis of chiral 2-acyl pyridines and pyrazines is reported. The strategy in- volves the metal–Lewis acid activation of acetyl aza-arenes and the secondary-amine activation of enals. The proposed mechanism is supported by DFT calculations. Funding Information: M.M. and R.R are grateful for EPSRC Core Capability Funding (EP/K039466/1). Financial contribution was received by A.M., M.M., and C.P. from the University of Bologna (RFO funds 2015 and 2016). Publisher Copyright: © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2018/9/6

Y1 - 2018/9/6

N2 - A novel catalytic enantioselective methodology based on synergistic catalysis for the synthesis of chiral 2-acyl pyridines and pyrazines is reported. The strategy involves the metal–Lewis acid activation of acetyl aza-arenes and the secondary-amine activation of enals. The proposed mechanism is supported by DFT calculations.

AB - A novel catalytic enantioselective methodology based on synergistic catalysis for the synthesis of chiral 2-acyl pyridines and pyrazines is reported. The strategy involves the metal–Lewis acid activation of acetyl aza-arenes and the secondary-amine activation of enals. The proposed mechanism is supported by DFT calculations.

KW - acetyl aza-arenes

KW - enals

KW - Michael addition

KW - secondary amine catalysis

KW - synergistic catalysis

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DO - 10.1002/chem.201802303

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JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 50

ER -

Synergistic Catalysis: Highly Enantioselective Acetyl Aza-arene Addition to Enals

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Keywords

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