Stereoelectronic control in Diels-Alder reaction of dissymmetric 1, 3-dienes.
The Diels-Alder reaction is a widely employed protocol in which four stereogenic centers are generated in a predictable manner with olefin geometry, adjoining chiral center, and transition-state topology serving as the main controlling elements. However, when the Diels-Alder partners are in a dissymmetric environment, pi-face selection is determined through the interplay of steric, orbital, and electrostatic factors whose relative importance is a subject of intense debate. Several new systems have been crafted to probe the mechanistic nuances of the pi-face selection. The available data have enabled us to qualitatively define a hierarchy of various stereoelectronic effects that would aid predictability of the stereochemical outcome.
Mehta
G
G
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India.
Uma
R
R
D003517:Cyclopentanes / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D011789:Quantum Theory
D003517:Cyclopentanes