38.06 The Endo Rule: Diastereoselectivity in the Diels-Alder Reaction

Defining endo and exo products. Introduction of the endo rule for determining the major product. Defining secondary orbital interactions and drawing them in the endo transition state. Secondary orbital interactions as a subtle kind of electron flow. The endo rule is most robust for p-orbital-containing substituents with either nonbonding lone pairs or multiple bonds.

00:00 Endo and Exo Diastereomers
01:39 The Endo Rule
02:17 Drawing the Endo and Exo Transition States
04:25 Depicting Secondary Orbital Interactions with Endo Substituents
06:42 Pi-containing Substituents Prefer the Endo Orientation
07:51 Summary

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