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Origin of stereoselectivities in asymmetric alkoxyselenenylations

Xue Wang, KN Houk, Martin Spichty, and Thomas Wirth (1999)

Journal of the American Chemical Society, 121(37):8567–8576.

Asymmetric alkoxyselenenylations of alkenes have been studied by B3LYP/3-21G, B3LYP/6-31G*, and SCI-PCM calculations. Stereoselectivities can be rationalized by the relative stabilities of transition states for attack of nucleophiles on seleniranium intermediates. A model to explain and predict stereoselectivities has been developed.

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