N-Carbamate protected amino acid derived guanidine organocatalysts

DOI: 10.1016/j.tet.2021.132093

Authors: Zahraa S. Al-Taie (Al-Nahrain University; Bangor University) , Joseph M. Anderson (Bangor University) , Laura Bischoff (Bangor University) , Jeppe Christensen (Diamond Light Source; University of Southampton) , Simon J. Coles (University of Southampton) , Richard Froom (Bangor University) , Mari E. Gibbard (Bangor University) , Leigh F. Jones (University of Wolverhampton) , F. F. J. De Kleijne (Bangor University) , Patrick J. Murphy (Bangor University) , Emma C. Thompson (Bangor University)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Tetrahedron , VOL 10

State: Published (Approved)
Published: April 2021

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 catalyst are lead compounds for the further development of this methodology.

Journal Keywords: Organocatalysis; amino acids; guanidines; H-bonded extended networks

Subject Areas: Chemistry


Technical Areas:

Added On: 07/04/2021 09:47

Discipline Tags:

Physical Chemistry Catalysis Chemistry Organic Chemistry

Technical Tags: