Asymmetric aza-Diels-Alder reaction of Danishefsky's diene with imines in a chiral reaction medium

Acid-free aza Diels-Alder reaction of Danishefsky's diene with imines.

[reaction: see text] A highly efficient aza Diels-Alder reaction of Danishefsky's diene with imines was found to occur in methanol in the absence of any acids at room temperature to give corresponding 2-substituted dihydro-4-pyridone derivatives in high yields. This reaction can be also carried out in a three-component one-pot reaction manner. The reaction was found to proceed through a Mannich...

An N,N'-dioxide/In(OTf)3 catalyst for the asymmetric Hetero-Diels-Alder reaction between Danishefsky's dienes and aldehydes: application in the total synthesis of triketide.

Asymmetric Brønsted acid-catalyzed aza-Diels–Alder reaction of cyclic C-acylimines with cyclopentadiene

A new chiral Brønsted acid-catalyzed aza-Diels-Alder reaction of cyclic C-acylimines with cyclopentadiene has been developed. The reaction provides optically active aza-tetracycles in good yields with high diastereo- and enantioselectivities under mild reaction conditions.

Synthesis of 2,5-disubstituted octahydroquinolin-4-ones via anintramolecular hetero Diels-Alder reaction.

A route for the preparation of 2,5-disubstituted octahydroquinolin-4-ones, synthetic precursors of the decahydroquinoline-type toxins, is presented. The key steps are an asymmetric epoxidation and an intramolecular hetero Diels-Alder reaction between an activated diene and an imine. The presence of an allylic stereogenic center induces some selectivity and thus only two cycloadducts are obtaine...

An asymmetric normal-electron-demand aza-Diels-Alder reaction via trienamine catalysis.

An asymmetric normal-electron-demand aza-Diels-Alder cycloaddition of 2-aryl-3H-indol-3-ones and 2,4-dienals was explored via trienamine catalysis of a chiral secondary amine. Multifunctional tricyclic polyhydropyrido[1,2-a]indoles were efficiently constructed in good stereoselectivity (up to 92% ee, >19 : 1 dr).