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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
(1R,6R)-1-Methyl-8-aza-spiro-[5.6]dodecan-7-one
Stéphanie M Guéret1, Ka Wai Choi, Patrick D O'Connor
1Department of Chemistry, Univerisity of Auckland, Private Bag 92019, Auckland, New Zealand.
Abstract:
The crystal structure of the title compound, C(12)H(21)NO, has been investigated to establish the absolute stereochemistry at position 1. The absolute stereochemistry at the quaternary centre at position 6 is established to be R using an asymmetric Birch reductive alkyl-ation reaction for which the stereochemical outcome is known. The crystal structure indicates the presence of two conformers of the bicyclic (1R,6R)-spiro-lactam ring system that differ in the conformation adopted by the six-membered ring. In one conformer, the meth-yl group adopts an axial position whereas in the other conformer, the same methyl group adopts an equatorial position. In both conformers, the seven-membered ring adopts a chair conformation. The two conformers of the bicyclic spiro-lactam are connected to each other via inter-molecular N-H⋯O hydrogen bonds forming a heterodimer. The asymmetric unit contains two such dimers.
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