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Intramolecular reaction
About: Intramolecular reaction is a research topic. Over the lifetime, 5015 publications have been published within this topic receiving 138213 citations.
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TL;DR: It has been further demonstrated that the IMDA reaction of vinylallenes is a versatile and convenient method to construct a wide range of polycycles.
Abstract: Rate studies have explored the effects of tether gem-dialkyl groups, allenyl substituents, fused ring size, and tether length on the intramolecular Diels-Alder reaction of vinylallenes. Additional new data on the «tert-butyl effect» has been provided. Mechanistic insight into the reaction has been developed which we hope will extend beyond the specific processes described herein. Finally, it has been further demonstrated that the IMDA reaction of vinylallenes is a versatile and convenient method to construct a wide range of polycycles
42 citations
TL;DR: In this article, the intramolecular cyclization reaction of primary or secondary alkenylzincs leads to a cyclopentylmethylzinc derivatives in a totally regiospecific 5-exo-trig cyclization in the presence of a highly sensitive function.
42 citations
TL;DR: In this paper, tert-butyl-substituted allyl malonates are diazotized in high yields to give 1-(tertbutoxycarbonyl)-3-oxa-2-oxobicyclo[3.1]hexanes.
Abstract: tert-Butyl-substituted allyl malonates, prepared in two steps from malonic acid, are diazotized in high yields. The diazomalonates 7 undergo a stereospecific copper(I)-catalyzed cyclopropanation to give 1-(tert-butoxycarbonyl)-3-oxa-2-oxobicyclo[3.1.0]hexanes 8 which can be converted to the protected (E)- or (Z)-1-aminocyclopropane-1-carboxylic acids 10 or 16 via Curtius- or Hoffman-type rearrangements, respectively. The sequences are short (six steps from malonic acid) and proceed with good overall yields (20-40% overall from malonic acid)
42 citations
TL;DR: In this paper, a single step synthesis of indole-annulated pentacyclic indolylhydroquinolines via tandem C-alkylation and intramolecular S-kylation of indolin-2-thiones with Nalkylquinolinium salts in excellent yields was reported.
42 citations
TL;DR: A novel method for the synthesis of phthalides and 3,4-dihydroisocoumarins via the palladium-catalyzed intramolecular benzannulation of bis-enyne and enyne-diyne systems is described.
Abstract: A novel method for the synthesis of phthalides and 3,4-dihydroisocoumarins via the palladium-catalyzed intramolecular benzannulation of bis-enyne and enyne-diyne systems is described. Various kinds of substituted phthalides 9 and 17 and 3,4-dihydroisocoumarins 19 were synthesized from 8, 16, and 18, respectively, in moderate to excellent yields. The benzannulation reaction proceeded chemoselectively to give the corresponding fused ring compounds A without the formation of the regioisomeric products B (eq 6). Furthermore, this methodology was applied to the synthesis of biologically active 3-n-butylphthalide 23.
42 citations