Concepedia

Tandem Hetero Diels−Alder Reaction:  Synthesis of Oxygenated Macrocycles

Brian R. Bear, Kenneth J. Shea

Organic Letters · 2001 · 13 citations · 9 references

DOI

Concepts

Abstract

[structure: see text]. C2-symmetric, oxygenated macrocycles have been synthesized from simple acyclic precursors in a single step by a tandem hetero Diels-Alder reaction. Thermolysis and Lewis acid catalysis can effect this novel transformation. The tandem reaction product is formed in preference to the intramolecular cycloaddition product, and an explanation for this result is proposed.

References

9

Enantioselective Synthesis of Dihydropyrans. Catalysis of Hetero Diels−Alder Reactions by Bis(oxazoline) Copper(II) Complexes

David A. Evans, Jeffrey S. Johnson, Edward J. Olhava · Journal of the American Chemical Society · 2000 · 318 citations

, , +13

Recent developments in the synthesis, structure and chemistry of bridgehead alkenes

Kenneth J. Shea · Tetrahedron · 1980 · 161 citations

, , +7

Highly Enantioselective Catalytic Hetero-Diels-Alder Reaction with Inverse Electron Demand

Jacob Thorhauge, Mogens Johannsen, Karl Anker Jørgensen · Angewandte Chemie International Edition · 1998 · 140 citations

, , +13

Intra- and intermolecular hetero-Diels-Alder reactions. 23. Intermolecular hetero-Diels-Alder reactions of enamino ketones at high pressure. The first significant pressure-induced diastereoselectivity in organic transformations

Lutz F. Tietze, T. HUEBSCH, Michael Buback et al. · Journal of the American Chemical Society · 1988 · 79 citations

, , +8

Accelerated inverse electron demand Diels-Alder reactions of 1-oxa-1,3-butadienes: [4 + 2] cycloaddition reactions of .beta.,.gamma.-unsaturated .alpha.-keto esters

Dale L. Boger, Kirk Robarge · The Journal of Organic Chemistry · 1988 · 69 citations

, , +9