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Ring opening of aziridine with PhMgX
Rhodium:
This reaction would be very interesting if it works not only for aromatic aziridines, but also for alkyl-aziridines:
First examples of C-arylation of aziridines catalyzed by indium triflate
J. S. Yadav, B. V. Subba Reddy, R. Srinivasa Rao, G. Veerendhar and K. Nagaiah
Tetrahedron Letters 42, 8067–8070 (2001) (https://www.thevespiary.org/rhodium/Rhodium/pdf/c-arylation.aziridines.in-triflate.pdf)
DOI:10.1016/S0040-4039(01)01699-9
Abstract
Aziridines react smoothly with arenes in the presence of a catalytic amount of indium triflate at ambient temperature to afford the corresponding -aryl amine derivatives in excellent yields with high regioselectivity.
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Also see Patent US6127550 where (chiral) beta-aminoalcohols are treated with TsCl/NaOH(aq) to form the corresponding N-Ts-Aziridines, which are then ring-opened by the reaction with Phenyllithium, to form the corresponding (chiral) alpha-substituted phenethylamines.
Rhodium:
Two-Carbon Homologation of Grignard Reagents to Primary Amines
K. Osowska-Pacewicka, A. Zwierzak
Synthesis 333-335 (1996) (https://www.thevespiary.org/rhodium/Rhodium/chemistry/grignard.aminoethylation.html)
Abstract
A novel, convenient synthesis of N-(diethoxyphosphoryl)aziridine is described. Application of this compound as a synthetic equivalent of an a2 type synthon for aminoethylation of Grignard reagents is demonstrated.
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