Applications of Dainshefsky's Dienes in the Asymmetric synthesis of Aza‐Diels‐Alder Reaction

Abstract

Asymmetric hetero-Diels-Alder (AHDA) reactions provide a multitude of opportunities for the highly efficient, regio- and stereoselective construction of various heterocycles in enantiomerically pure form. The asymmetric aza-Diels-Alder (A-aza-DA) reaction using diversely hetero-dienophiles and hetero-dienes have been increasingly developed as a valuable method for the synthesis of functionalized nitrogen ring systems. The purpose of this review is to give a detailed discussion of the A-aza-DA reaction particularly, the stereoselective reactions of imines as dienophiles with Dainshefsky dienes to obtain optically pure aza-Diels-Alder products. The development of stereoselective variants of the reaction make use of imines as the dienophile and Dainshefsky dienes is at the forefront of these studies. This review updates the A-aza-DA reactions covering the literature from 1972 till date.

Prescribed drugs containing nitrogen heterocycles: an overview

“…[25][26][27][28][29][30][31][32][33] In recent years, our group has also focused on the applications of name reactions in the total synthesis of natural products containing nitrogen heterocycles, showing diverse biological activities. [34][35][36][37][38][39][40][41][42] Armed with these experiences, in this review we try to highlight the medical usages and selected synthetic pathways of approved and market purchasable prescribed medications, containing nitrogen based-heterocycles. Having collected and categorized of about 640 medications, comprising a based-nitrogen heterocycle, we had to be selective and sumarritive, limiting ourselves to most common of such pharmaceuticals, classifying them in accordance of their size of N-based heterocycles, in, four, ve, six, and seven-membered rings.…”

Can Primary Arylamines Form Enamine? Evidence, α-Enaminone, and [3+3] Cycloaddition Reaction

“…It would be interesting to determine if a similar reaction could happen to α-enaminones. Aza-Diels–Alder reactions lead to nitrogen-containing heterocycles, which constitute one of the most important structural motifs in natural products, pharmaceuticals, and biosystems. ,− Incorporation of α-enaminones into ADARs would introduce an extra carbonyl group into the resulting heterocycles, opening new functionalization opportunities.…”

Catalytic Asymmetric Aza‐Diels‐Alder Reaction: Pivotal Milestones and Recent Applications to Synthesis of Nitrogen‐Containing Heterocycles

“…A majority of such reactions is based on the use of linear or cyclic electron‐rich dienes bearing alkyl, silyloxy or alkoxy groups (in particular, Danishefsky's [35,36] or Brassard's [37] dienes), and enamine or enolate fragments. Electron‐poor nitrogen‐containing dienophiles commonly serve as starting substrates [38,39] .…”