Highly Enantioselective Synthesis of Alkylpyridine Derivatives through a Michael/Michael/Aldol Cascade Reaction

Marta Meazza; Michael Potter; Mateusz B. Pitak; Simon J. Coles; Andrea Mazzanti; Ramon Rios

doi:10.1002/ejoc.201601491

Highly Enantioselective Synthesis of Alkylpyridine Derivatives through a Michael/Michael/Aldol Cascade Reaction

Marta Meazza
, Michael Potter
, Mateusz B. Pitak
, Simon J. Coles
, Andrea Mazzanti
, Ramon Rios

Chemistry

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

10 Scopus citations

Abstract

A method for the synthesis of pyridine derivatives based on a triple cascade reaction catalyzed by chiral secondary amines was developed. The resulting cyclohexenes (three C–C bonds were formed) were obtained in good yields with good diastereoselectivities and excellent enantioselectivities.

Original language	British English
Pages (from-to)	719-725
Number of pages	7
Journal	European Journal of Organic Chemistry
Volume	2017
Issue number	3
DOIs	https://doi.org/10.1002/ejoc.201601491
State	Published - 18 Jan 2017

Keywords

Domino reactions
Enantioselectivity
Michael addition
Nitrogen heterocycles
Organocatalysis

Access to Document

10.1002/ejoc.201601491

OpenUrl availability

Full text

Cite this

@article{8ffb23fb473847839d994477e32ff67f,

title = "Highly Enantioselective Synthesis of Alkylpyridine Derivatives through a Michael/Michael/Aldol Cascade Reaction",

abstract = "A method for the synthesis of pyridine derivatives based on a triple cascade reaction catalyzed by chiral secondary amines was developed. The resulting cyclohexenes (three C–C bonds were formed) were obtained in good yields with good diastereoselectivities and excellent enantioselectivities.",

keywords = "Domino reactions, Enantioselectivity, Michael addition, Nitrogen heterocycles, Organocatalysis",

author = "Marta Meazza and Michael Potter and Pitak, \{Mateusz B.\} and Coles, \{Simon J.\} and Andrea Mazzanti and Ramon Rios",

note = "Funding Information: M. M. and R. R. acknowledge the European Regional Development Fund (ERDF) for co-financing the AI-CHEM-Chem. project (no. 4061) through the INTERREG IV A France (Channel) – England cross-border cooperation program. M. M., M. P., and R. R. are grateful for Engineering and Physical Sciences Research Council (EPSRC) core capability funding (EP/K039466/1). A. M. thanks the University of Bologna (RFO-2014 funds). We thank Diamond Light Source for the allocation of beam time MT8521 on beamline I19. Publisher Copyright: {\textcopyright} 2017 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2017",

month = jan,

day = "18",

doi = "10.1002/ejoc.201601491",

language = "British English",

volume = "2017",

pages = "719--725",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

number = "3",

}

TY - JOUR

T1 - Highly Enantioselective Synthesis of Alkylpyridine Derivatives through a Michael/Michael/Aldol Cascade Reaction

AU - Meazza, Marta

AU - Potter, Michael

AU - Pitak, Mateusz B.

AU - Coles, Simon J.

AU - Mazzanti, Andrea

AU - Rios, Ramon

N1 - Funding Information: M. M. and R. R. acknowledge the European Regional Development Fund (ERDF) for co-financing the AI-CHEM-Chem. project (no. 4061) through the INTERREG IV A France (Channel) – England cross-border cooperation program. M. M., M. P., and R. R. are grateful for Engineering and Physical Sciences Research Council (EPSRC) core capability funding (EP/K039466/1). A. M. thanks the University of Bologna (RFO-2014 funds). We thank Diamond Light Source for the allocation of beam time MT8521 on beamline I19. Publisher Copyright: © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2017/1/18

Y1 - 2017/1/18

N2 - A method for the synthesis of pyridine derivatives based on a triple cascade reaction catalyzed by chiral secondary amines was developed. The resulting cyclohexenes (three C–C bonds were formed) were obtained in good yields with good diastereoselectivities and excellent enantioselectivities.

AB - A method for the synthesis of pyridine derivatives based on a triple cascade reaction catalyzed by chiral secondary amines was developed. The resulting cyclohexenes (three C–C bonds were formed) were obtained in good yields with good diastereoselectivities and excellent enantioselectivities.

KW - Domino reactions

KW - Enantioselectivity

KW - Michael addition

KW - Nitrogen heterocycles

KW - Organocatalysis

UR - https://www.scopus.com/pages/publications/85010674442

U2 - 10.1002/ejoc.201601491

DO - 10.1002/ejoc.201601491

M3 - Article

AN - SCOPUS:85010674442

SN - 1434-193X

VL - 2017

SP - 719

EP - 725

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 3

ER -

Highly Enantioselective Synthesis of Alkylpyridine Derivatives through a Michael/Michael/Aldol Cascade Reaction

Abstract

Keywords

Access to Document

OpenUrl availability

Other files and links

Fingerprint

Cite this