Summary.
The easily available cycloalkanoyl acetic- and propionic acid esters are transformed to the corresponding amines by standard procedures. These in turn provided an efficient access to cyclic α-aminonitriles, which were reacted with a series of Grignard reagents yielding stereoselectively the cis-configured title compounds; the scope and limitation of this route were investigated. The stereochemical assignment was achieved by X-ray crystallography and NMR spectroscopy.
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Part of PhD thesis, LMU München, D
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Reimann, E., Ettmayr, C. & Polborn, K. Angularly Substituted Octahydroindoles, Decahydroquinolines, Octahydropyrindines, and Octahydrocyclopenta[b]pyrroles by Bruylants Reaction. Monatshefte für Chemie 135, 557–579 (2004). https://doi.org/10.1007/s00706-003-0136-8
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DOI: https://doi.org/10.1007/s00706-003-0136-8