Reverse-electron-demand diels-alder dienophile π-face selectivity via conformation dependent transmission of π-σ-π electronic interactions.

✍ Scribed by J.Gabriel Garcia; Mark L. McLaughlin

• Publisher: Elsevier Science
• Year: 1991
• Tongue: French
• Weight: 263 KB
• Volume: 32
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)92689-3

✦ Synopsis

Reverse-electron-demand Diels-Alder reactions of a series of remotely substituted cyclooctenes with hexachlorocyclopentadiene and 5,5-dimethoxy-1,2,3,4-tetrachlorocyclopenta-2,4-diene indicate that dienophile aface selectivity results from conformation dependent transmission of x-o-n electronic interactions. Paquette and others have attributed Diels-Alder diene x-face selectivity to cr-7c electronic interactions1 and Gugelchuk has reported long-range electronic control of Die&Alder diene n-face stereoselection.

Hoffman,