N-carbamate protected amino acid derived guanidine organocatalysts

Zahraa S. Al-Taie; Joseph M. Anderson; Laura Bischoff; Jeppe Christensen; Simon J. Coles; Richard Froom; Mari E. Gibbard; Leigh F. Jones; Frank F. J. de Kleijne; Paddy Murphy; Emma  Thompson

doi:10.1016/j.tet.2021.132093

N-carbamate protected amino acid derived guanidine organocatalysts

Zahraa S. Al-Taie, Joseph M. Anderson, Laura Bischoff, Jeppe Christensen, Simon J. Coles, Richard Froom, Mari E. Gibbard, Leigh F. Jones, Frank F. J. de Kleijne, Paddy Murphy, Emma Thompson

School of Environmental & Natural Sciences

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Abstract

We report the preparation of a range of N-protected amino acid derived guanidine organocatalysts and their application to the Michael addition of 2-hydroxy-1,4-napthoquinone to β-nitrostyrene, achieving a maximum ee of 26%. Whilst these catalysts gave poor ees, the structural variation together with the X-ray crystallographic study of the intra- and intermolecular hydrogen bonding reported suggest that the C2-symmetric catalysts are lead compounds for the further development of this methodology.

Original language	English
Article number	132093
Journal	Tetrahedron
Volume	89
Early online date	2 Apr 2021
DOIs	https://doi.org/10.1016/j.tet.2021.132093
Publication status	Published - 4 Jun 2021

Keywords

Amino acids
Guanidines
H-bonded extended networks
Organocatalysis

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10.1016/j.tet.2021.132093

2021 N-carbamate protected amino acid derived guanidine organocatalystsAccepted author manuscript, 4.78 MBLicence: CC BY-NC-ND

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title = "N-carbamate protected amino acid derived guanidine organocatalysts",

abstract = "We report the preparation of a range of N-protected amino acid derived guanidine organocatalysts and their application to the Michael addition of 2-hydroxy-1,4-napthoquinone to β-nitrostyrene, achieving a maximum ee of 26\%. Whilst these catalysts gave poor ees, the structural variation together with the X-ray crystallographic study of the intra- and intermolecular hydrogen bonding reported suggest that the C2-symmetric catalysts are lead compounds for the further development of this methodology.",

keywords = "Amino acids, Guanidines, H-bonded extended networks, Organocatalysis",

author = "Al-Taie, \{Zahraa S.\} and Anderson, \{Joseph M.\} and Laura Bischoff and Jeppe Christensen and Coles, \{Simon J.\} and Richard Froom and Gibbard, \{Mari E.\} and Jones, \{Leigh F.\} and \{de Kleijne\}, \{Frank F. J.\} and Paddy Murphy and Emma Thompson",

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month = jun,

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doi = "10.1016/j.tet.2021.132093",

language = "English",

volume = "89",

journal = "Tetrahedron",

issn = "0040-4020",

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TY - JOUR

T1 - N-carbamate protected amino acid derived guanidine organocatalysts

AU - Al-Taie, Zahraa S.

AU - Anderson, Joseph M.

AU - Bischoff, Laura

AU - Christensen, Jeppe

AU - Coles, Simon J.

AU - Froom, Richard

AU - Gibbard, Mari E.

AU - Jones, Leigh F.

AU - de Kleijne, Frank F. J.

AU - Murphy, Paddy

AU - Thompson, Emma

PY - 2021/6/4

Y1 - 2021/6/4

N2 - We report the preparation of a range of N-protected amino acid derived guanidine organocatalysts and their application to the Michael addition of 2-hydroxy-1,4-napthoquinone to β-nitrostyrene, achieving a maximum ee of 26%. Whilst these catalysts gave poor ees, the structural variation together with the X-ray crystallographic study of the intra- and intermolecular hydrogen bonding reported suggest that the C2-symmetric catalysts are lead compounds for the further development of this methodology.

AB - We report the preparation of a range of N-protected amino acid derived guanidine organocatalysts and their application to the Michael addition of 2-hydroxy-1,4-napthoquinone to β-nitrostyrene, achieving a maximum ee of 26%. Whilst these catalysts gave poor ees, the structural variation together with the X-ray crystallographic study of the intra- and intermolecular hydrogen bonding reported suggest that the C2-symmetric catalysts are lead compounds for the further development of this methodology.

KW - Amino acids

KW - Guanidines

KW - H-bonded extended networks

KW - Organocatalysis

U2 - 10.1016/j.tet.2021.132093

DO - 10.1016/j.tet.2021.132093

M3 - Article

SN - 0040-4020

VL - 89

JO - Tetrahedron

JF - Tetrahedron

M1 - 132093

ER -

N-carbamate protected amino acid derived guanidine organocatalysts

Abstract

Keywords

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