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

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

The asymmetric aza-Diels-Alder reaction of chiral imines with Danishefsky's diene in chiral ionic liquids provides the corresponding cycloadduct with moderate to high diastereoselectivity. The reaction has proved to perform better at room temperature in ionic liquids without either Lewis acid catalyst or organic solvent. Chiral ionic liquids are recycled while their efficiency is preserved.

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.

A new route for the synthesis of highly substituted 4-aminoquinoline drug like molecules via aza hetero-Diels-Alder reaction.

We have demonstrated for the first time the use of 2H-indazole as a diene partner in an aza hetero-Diels-Alder reaction leading to highly substituted 4-aminoquinolines via a heterocylic-heterocylic (H-H) strategy and have further developed a tandem one-pot method starting from 2-azidobenzaldehyde by the formation of 2C-N, 1N-N and 1C-C bonds. The key features of the present protocol are readily...

A competitive Diels-Alder/1, 3-dipolar cycloaddition reaction of1-H-imidazole 3-oxide toward sulfonyl methane. A DFT study on the energetic and regioselectivity

The dual diene/1,3-dipolar character of 1-H-imidazole 3-oxide, HIO 1, allows this compound toparticipate in a competitive Diels-Alder (DA)/1,3-dipolar cycloaddition (13DC) reaction toward C=Sdouble bond of the electro-deficient sulfonyl methane SFM 2. The B3LYP/6-311++G(d,p) calculatedrelative Gibbs free energies indicate that among the studied 13DC and DA reactions, former iscompletely preferr...

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...