Abstract
1,5‐Benzothiazepine frameworks are highly relevant in medicinal chemistry. Reported catalytic asymmetric approaches to these scaffolds have targeted 2,3‐dihydro‐1,5‐benzothiazepin‐4‐ones but leave the corresponding amines (i.e., 2,3,4,5‐tetrahydro‐1,5‐benzothiazepines) out of reach. Herein, we present the first entry to these important compounds in enantioenriched form. Our approach is based on the catalytic asymmetric sulfa‐Michael addition of 2‐aminothiophenols to trans‐chalcones, followed by intramolecular reductive amination. Both reactions required careful study to solve several challenging issues. The resulting optimized two‐step protocol afforded a range of 2,3,4,5‐tetrahydro‐1,5‐benzothiazepines as single trans diastereomers in moderate to good yields and enantioselectivities.
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