N-carbamate protected amino acid derived guanidine organocatalysts

TETRAHEDRON

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Article

Al-Taie, Zahraa S.^1,2  Anderson, Joseph M.²  Bischoff, Laura²  Christensen, Jeppe^3,4  Coles, Simon J.⁴  Froom, Richard²  Gibbard, Mari E.²  Jones, Leigh F.⁵  de Kleijne, Frank F. J.²  Murphy, Patrick J.²  Thompson, Emma C.² 

[1] Al Nahrain Univ, Coll Sci, Dept Chem, Baghdad, Iraq

[2] Bangor Univ, Sch Nat Sci Chem, Bangor LL57 2UW, Gwynedd, Wales

[3] Diamond Light Source, Didcot OX12 0DE, Oxon, England

[4] Univ Southampton, Sch Chem, EPSRC Natl Crystallog Serv, Southampton SO17 1BJ, Hants, England

[5] Univ Wolverhampton, Sch Biol Phys & Forens Sci, Wolverhampton WV1 1LY, England

关键词: Organocatalysis;    Amino acids;    Guanidines;    H-bonded extended networks;   

DOI  :  10.1016/j.tet.2021.132093

来源: Elsevier

【 摘 要 】

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 beta-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 C-2-symmetric catalysts are lead compounds for the further development of this methodology. (C) 2021 Published by Elsevier Ltd.

【 授权许可】

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