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N-carbamate protected amino acid derived guanidine organocatalysts

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

Standard Standard

N-carbamate protected amino acid derived guanidine organocatalysts. / Al-Taie, Zahraa S.; Anderson, Joseph M.; Bischoff, Laura et al.
In: Tetrahedron, Vol. 89, 132093, 04.06.2021.

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

HarvardHarvard

Al-Taie, ZS, Anderson, JM, Bischoff, L, Christensen, J, Coles, SJ, Froom, R, Gibbard, ME, Jones, LF, de Kleijne, FFJ, Murphy, P & Thompson, E 2021, 'N-carbamate protected amino acid derived guanidine organocatalysts', Tetrahedron, vol. 89, 132093. https://doi.org/10.1016/j.tet.2021.132093

APA

Al-Taie, Z. S., Anderson, J. M., Bischoff, L., Christensen, J., Coles, S. J., Froom, R., Gibbard, M. E., Jones, L. F., de Kleijne, F. F. J., Murphy, P., & Thompson, E. (2021). N-carbamate protected amino acid derived guanidine organocatalysts. Tetrahedron, 89, Article 132093. https://doi.org/10.1016/j.tet.2021.132093

CBE

Al-Taie ZS, Anderson JM, Bischoff L, Christensen J, Coles SJ, Froom R, Gibbard ME, Jones LF, de Kleijne FFJ, Murphy P, et al. 2021. N-carbamate protected amino acid derived guanidine organocatalysts. Tetrahedron. 89:Article 132093. https://doi.org/10.1016/j.tet.2021.132093

MLA

Al-Taie, Zahraa S. et al. "N-carbamate protected amino acid derived guanidine organocatalysts". Tetrahedron. 2021. 89. https://doi.org/10.1016/j.tet.2021.132093

VancouverVancouver

Al-Taie ZS, Anderson JM, Bischoff L, Christensen J, Coles SJ, Froom R et al. N-carbamate protected amino acid derived guanidine organocatalysts. Tetrahedron. 2021 Jun 4;89:132093. Epub 2021 Apr 2. doi: 10.1016/j.tet.2021.132093

Author

Al-Taie, Zahraa S. ; Anderson, Joseph M. ; Bischoff, Laura et al. / N-carbamate protected amino acid derived guanidine organocatalysts. In: Tetrahedron. 2021 ; Vol. 89.

RIS

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

VL - 89

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

M1 - 132093

ER -