Advances in Organic Synthesis

Volume: 5

Regio- and Stereoselective Ring Opening of Allylic Epoxides

Author(s): Mauro Pineschi, Ferruccio Bertolini, Valeria Di Bussolo and Paolo Crotti

Pp: 101-184 (84)

DOI: 10.2174/9781608054800113050005

* (Excluding Mailing and Handling)


Three-membered heterocyclic rings offer a powerful combination of reactivity, stability, availability, and atom economy. In fact, the asymmetric ring opening of allylic epoxides with nucleophiles of different kinds, as will be discussed in this Review, offers the possibility of generating valuable chiral non-racemic building blocks in a very simple manner and in a stereodefined fashion.

Keywords: Allylic epoxides, nucleophilic ring opening, heteronucleophiles, carbon nucleophiles, regioselectivity, stereoselectivity, enantioselectivity.

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