Origin of stereoselectivity in the reduction of a planar oxacarbenium |
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Authors: | Um Joann M Houk K N Phillips Andrew J |
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Institution: | Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA. |
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Abstract: | The Kishi reduction of a planar oxacarbenium was investigated theoretically. The high diastereoselectivity for hydride transfer to the oxacarbenium intermediate is attributed to the conformation of the transition state that places the allyl side chain in an equatorial position in the major transition state and axial position in the minor. The minor transition state is destabilized by a 1,3-diaxial strain between the attacking hydride and the syn allyl side chain. |
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