Asymmetric induction in the allylic rearrangement of chiral amine oxide
- 1 January 1973
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 22,p. 848-849
- https://doi.org/10.1039/c39730000848
Abstract
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.Keywords
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