Tetrahedron: Asymmetry

… N-3, 4-dimethoxyphenethyl derivatives of the 1-phenyl ethanolamines halostachine, ephedrine and pseudoephedrine to 1-phenyl-N-methyl-7, 8-dimethoxy-1, 2, 4, 5- …

SJ Coote, SG Davies, D Middlemiss, A Naylor

Index: Coote, Steven J.; Davies, Stephen G.; Middlemiss, David; Naylor, Alan Tetrahedron: Asymmetry, 1990 , vol. 1, # 1 p. 33 - 56

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Citation Number: 28

Abstract

Abstract Acid promoted cyclisation of homochiral (R)-N-(3, 4-dimethoxyphenethyl)- halostachine proceeds with almost total racemisation to yield 1-phenyl-N-methyl-1, 2, 4, 5- tetrahydrobenz [d] azepine (ee 6%). Coordination of the cyclisation precursor to the tricarbonylchromium (0) moiety renders the cyclisation completely stereospecific to afford, after decomplexation, homochiral (+)-(R)-1-phenyl-N-methyl-1, 2, 4, 5-tetrahydrobenz [d] ...