Sythesis and Stereochemistry of 11-Amino-6, 6a, 7, 8, 9, 10, 10a, 11-octahydrodibenzo[b, e]thiepines and-oxepines

Abstract

11-Amino-6, 6a, 7, 8, 9, 10, 10a, 11-octahydrodibebenzo[b, e]thiepines (6a-d) and -oxepines (7a-d) were synthesized by the Leuckart reaction of 6, 6a, 7, 8, 9, 10, 10a, 11-octahydro-11-oxodibenzo[b, e]thiepines (1a, b)and -oxepines (2a, b) followed by hydrolysis of the reaction products 4a-d and 5a-d, respectively. The four diastereomers, cis(6a-H, 10a-H)-cis(10a-H, 11-H) 6a and 7a, cis(6a-H, 10a-H)-trans(10a-H, 11-H) 6b and 7b, trans(6a-H, 10a-H)-trans(10a-H, 11a-H)6c and 7c, and trans(6a-H, 10a-H)-cis(10a-H, 11-H) 6d and 7d, were isolated and their configurations and conformations were elucidated by chemical methods together with ¹H-nuclear magnetic resonance spectroscopic and X-ray crystallographic analyses.