10. Patented Literature 2616 10.1. Esterification 2616 10.2. Ether Formation 2619 10.2.1. Etherification without Cyclization 2619 10.2.2. Etherification with Cyclization 2624 10.3. N-Alkylation 2625 10.4. Other Reactions 2627 11. Summary and Outlook 2628 12. Note Added in Proof 2628 13. Abbreviations Used in This Review 2629 14. Acknowledgments 2629 15. Supporting Information Available 2630 16. References 2630

Mitsunobu and Related Reactions: Advances and Applications

Metalated heterocycles and their applications in synthetic organic chemistry.

γ-Butenolides, γ-butyrolactones, and derivatives, especially in enantiomerically pure form, constitute the structural core of numerous natural products which display an impressive range of biological activities which are important for the development of novel physiological and therapeutic agents. Furthermore, optically active γ-butenolides and γ-butyrolactones serve also as a prominent class of chiral building blocks for the synthesis of diverse biological active compounds and complex molecules. Taking into account the varying biological activity profiles and wide-ranging structural diversity of the optically active γ-butenolide or γ-butyrolactone structure, the development of asymmetric synthetic strategies for assembling such challenging scaffolds has attracted major attention from synthetic chemists in the past decade. This review offers an overview of the different enantioselective synthesis of γ-butenolides and γ-butyrolactones which employ catalytic amounts of metal complexes or organocatalysts, wit...

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Catalytic Asymmetric Synthesis of Butenolides and Butyrolactones

Rearrangement reactions occupy a special place within the canon of organic synthesis, by virtue of the inherently high efficiency of chemical processes which form and break bonds by redistribution of electrons around a retained atomic framework. Within the broader class, sigmatropic rearrangements are chemical processes defined by mechanisms involving unimolecular migration of σ-bonds with concomitant redistribution of one or more π-bonds. Sigmatropic processes may involve uncharged or charged species, with the charges located on carbon or heteroatoms; the latter reaction type is the subject of this tutorial review.

Sigmatropic rearrangements of ‘onium’ ylids

Cycloisomerization of γ- and δ-acetylenic acids catalyzed by gold(I) chloride

Recent developments in the synthesis of furan-2(5H)-ones

[2,3]-Sigmatropic rearrangements of didehydropiperidinium ylids

Preparation and reactions of 3,4-bisstannyl-2(5H)furanones

A benzofuro[6,7-b]morphinan related to naltriben has been synthesised using a radical induced cyclisation of 6β-O-(2-bromophenyl)codeine, itself prepared by a Mitsunobu reaction between codeine and 2-bromophenol. A Stille coupling between codeine 6-O-trifluoromethanesulfonate and vinyltri(butyl)tin leads to a 6-deoxyvinyl-codeine derivative, which can be reacted with electron-poor dienophiles to afford 6,7-fused cycloadducts.

Neil B. Carter

Papers

Recent developments in the synthesis of furan-2(5H)-ones

[2,3]-Sigmatropic rearrangements of didehydropiperidinium ylids

Preparation and reactions of 3,4-bisstannyl-2(5H)furanones

The synthesis of some 6,7-annulated codeines

Recent Developments in the Synthesis of Furan-2(5H)-ones