Tricarbonylchromium(0) promoted stereoselective cyclisations of the 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-tetrahydrobenzazepines
作者： Steven J. Coote , Stephen G. Davies , David Middlemiss , Alan Naylor
DOI: 10.1016/S0957-4166(00)82268-5
关键词: Stereochemistry 、 Yield (chemistry) 、 Stereoselectivity 、 Stereospecificity 、 Moiety 、 Chemistry 、 Ethanolamines 、 Diastereomer 、 Halostachine 、 Azepine
摘要: 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 (e.e. 6%). Coordination the precursor tricarbonylchromium(0) moiety renders completely stereospecific afford, after decomplexation, (+)-(R)-1 -phenyl-N-methyl-1,2,4,5-tetrahydrobenz[d]azepine. (−)-(1R,2S)-N-(3,4-Dimethoxyphenethyl)ephedrine undergoes acid mediated furnish trans-(−)-(1R,2S)-1-phenyl-2-methyl-N-methyl-7,8-dimethoxy tetrahydrobenzazepine as a single diastereoisomer. In contrast, epimeric (−)-(1R,2R)-N-(3,4-dimethoxyphenethyl)pseudoephedrine cyclises give mixture (ratio 91:9) trans- and cis-1-phenyl-2-methyl-N-methyl-7,8-dimethoxy tetrahydrobenzazepine. However, complex of(−)-(1R,2R)-N-(3,4-dimethoxyphenethyl)pseudo-ephedrine is stercoselective trans-(+)-(1S,2R)-1-phenyl-2-methyl-N-methyl-7,8-dimethoxy decomplexation.
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