Advances in Organic Synthesis

Volume: 5

Indexed in: Scopus, EBSCO, Ulrich's Periodicals Directory

Advances in Organic Synthesis is a book series devoted to the latest advances in synthetic approaches towards challenging structures. It presents comprehensive articles written by eminent authorities ...
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Regio- and Stereoselective Ring Opening of Allylic Epoxides

Pp. 101-184 (84)

Mauro Pineschi, Ferruccio Bertolini, Valeria Di Bussolo and Paolo Crotti

Abstract

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.

Affiliation:

Dipartimento di Farmacia, Università di Pisa, via Bonanno 33, 56126, Pisa, Italy