The [2,3]-sigmatropic rearrangement of (R)-NN-dimethyl-3-(1-phenyl-phenyl-trans-but-1-enyl)amine oxide to give (S)-O-trans-1-phenyl-but-2-enyl-NN-dimethylhydroxyl-amine was effected thermally with nearly complete transfer of chirality from tetramally carbon to trigonal carbon via a cyclic half-chair transition state conformation.
Y. Yamamoto, J. Oda and Y. Inouye, J. Chem. Soc., Chem. Commun., 1973, 848 DOI: 10.1039/C39730000848
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