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New racemic vicinal amino alcohol derivatives with 4‐benzylidenecyclohexane skeleton and axial chirality have been prepared. A preparatively easy and efficient protocol for resolution of the N‐benzoylamino alcohol is described. Using a 250 × 20 mm (L × ID) Chiralpak® IA column, and the appropriate mixture of n‐hexane/ethanol/chloroform as eluent, both enantiomers of N‐benzoylamino alcohol 3 are obtained...
(1R,5S)‐2‐Methyl‐6,7‐benzomorphan has been synthesised from (R)‐(benzyloxy)(phenyl)acetaldehyde. On a 2‐mmol scale Bi (OTf)3 promoted Aza‐Prins reaction with N‐tosylhomoallylamine afforded an 88/12 mixture of 6‐oxa‐2‐azabicyclo[3.2.1]octanes. Major diastereoisomer was converted to enantiomerically pure (2S,4S)‐2‐benzyl‐1‐ methylpiperidin‐4‐ol via a high‐yielding sequence hydrogenolysis/N‐detosylation/N‐methylation...
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