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  • Title: Dithiane additions to vinyl epoxides: steric control over the SN2 and SN2' manifolds.
    Author: Smith AB, Pitram SM, Gaunt MJ, Kozmin SA.
    Journal: J Am Chem Soc; 2002 Dec 11; 124(49):14516-7. PubMed ID: 12465944.
    Abstract:
    High chemoselectivity can be achieved in the addition of lithium dithiane anions to vinyl epoxides exploiting the steric nature of the dithiane substituent. Unencumbered dithiane anions afford SN2 adducts, whereas sterically encumbered anions lead primarily to SN2' adducts. Furthermore, the SN2' addition occurs syn to the vinyl epoxide.
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