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Orbital Phase Environments and Stereoselectivities

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Orbitals in Chemistry

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 289))

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Abstract

Facial selections are reviewed to propose a new theory, orbital phase environment, for stereoselectivities of organic reactions. The orbital phase environment is a generalized idea of the secondary orbital interaction between the non-reacting centers and the unsymmetrization of the orbitals at the reacting centers arising from in-phase and out-of-phase overlap** with those at the neighboring non-reacting sites. In this context, the nucleophilic addition preferentially occurs on the face of the carbonyl functionality opposite to the better electron-donating orbital at the β position. In a similar manner to the carbonyl cases, the preferred reaction faces of olefins in electrophilic addition reactions are opposite to the better electron-donating orbitals at the β positions. The orbital phase environments in Diels-Alder reactions are also reviewed.

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  1. Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo, 113, Japan

    Tomohiko Ohwada

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Correspondence to Tomohiko Ohwada .

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  1. Fac. Engineering, Gifu University, Yanagido 1-1 , Gifu, 501-1193, Japan

    Satoshi Inagaki

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Ohwada, T. (2009). Orbital Phase Environments and Stereoselectivities. In: Inagaki, S. (eds) Orbitals in Chemistry. Topics in Current Chemistry, vol 289. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2008_38

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