Oxiranes and Oxirenes: Fused-ring Derivatives

D. M. Hodgson (1) , M. A. H. Stent (2) , M. K. Reilly (3) , E. Gras (4)

1 University of Oxford
2 Key Organics Ltd.
3 UC Irvine - University of California [Irvine]
4 LCC - Laboratoire de chimie de coordination

Advances, during the period 1995–2012, in the chemistry of oxiranes (epoxides) and oxirenes fused to other ring systems are presented. Particular emphasis is placed on advances in the asymmetric synthesis of ring-fused oxiranes (metallosalen catalyzed, chiral dioxirane, or iminium salt mediated) and the reactivity of such species (ring-opening reactions, the chemistry of lithiated epoxides). The chemistry of ring-fused oxirenes remains limited.

Mots clés: Asymmetric desymmetrization Carbenoids Chiral C–H Insertion Dioxiranes Epoxidation Epoxides Lithiooxirane Oxiranes Oxirenes Rearrangement Reductive alkylation Ring opening

Domaines: Chimie de coordination

D. M. Hodgson, M. A. H. Stent, M. K. Reilly, E. Gras. Oxiranes and Oxirenes: Fused-ring Derivatives. Reedijk, J. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering, 1, Elsevier, pp.235-298, 2014, Comprehensive Heterocyclic Chemistry III, 978-0-12-409547-2. ⟨hal-02042486⟩