Application of the intramolecular isomerisation-aldolisation from allylic alcohols and allylic silyl ethers to the synthesis of indanones and indenones.
A new access to indanones was discovered through a one-step nickel or iron-mediated transposition of 2-hydroxyisobenzofurans. Starting from the corresponding silylenol ethers, a new one-pot tandem isomerisation-Mukaiyama aldol process was also developed. These versatile strategies will be useful for the preparation of various types of indanones and indenones.
Petrignet
Julien
J
Synthèse et Electrosynthèse Organiques CNRS UMR 6510, Université de Rennes 1, Avenue du Général Leclerc, 35042 Rennes Cedex, France.
Roisnel
Thierry
T
Grée
René
R
D000438:Alcohols / Q000737:chemistry*; D000498:Allyl Compounds / Q000737:chemistry*; D001572:Benzofurans / Q000737:chemistry; D002384:Catalysis; D018360:Crystallography, X-Ray; D006868:Hydrolysis; D007189:Indans / Q000737:chemistry*; D007501:Iron / Q000737:chemistry; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D009532:Nickel / Q000737:chemistry; D013237:Stereoisomerism
D000438:Alcohols; D000498:Allyl Compounds; D001572:Benzofurans; D007189:Indans; D009532:Nickel; D007501:Iron