Evidence for C(1)–N(2) bond scission in the isomerization of cis-1,3-disubstituted Nb-benzyl-1,2,3,4-tetrahydro-β-carbolines into their trans diastereomers under acidic conditions
Chemical Communications Pub Date: 1900-01-01 DOI: 10.1039/CC9960002477
Abstract
When cis diastereomer 13a was stirred in CF3CO2D the trans isomer 13b ws isolated in 90% yield, while treatment of 13a with CF3CO2H–NaBH4 provided a mixture of the C(1)–N(2) cleaved product 14 and the trans isomer 13b; this provides the best evidence to date that scission of the C(1)–N(2) bond occurs during epimerization of cis-1,3-disubstituted 1,2,3,4-tetrahydro-β-carbolines such as 13a into their trans isomers 13b.
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Journal Name：Chemical Communications
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CAS no.: 89640-58-4
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