A Practical Titanium-Catalyzed Synthesis of Bicyclic Cyclopentenones and Allylic Amines
- 1 January 1996
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 61 (8) , 2713-2718
- https://doi.org/10.1021/jo951763l
Abstract
A practical titanium-catalyzed synthesis of bicyclic cyclopentenones and allylic amines is described. The process converts enyne substrates to iminocyclopentenes using 10 mol % of the air- and moisture-stable precatalyst Cp2TiCl2 in the presence of n-BuLi and triethylsilyl cyanide. The resulting iminocyclopentenes can be hydrolyzed to cyclopentenones in good yields or reduced to allylic silylamines with Red-Al or DIBALH. Treatment of the crude silylamines with acetyl chloride allows isolation of allylic amides in excellent yields.Keywords
This publication has 28 references indexed in Scilit:
- Cycloaddition of zirconacyclopentadienes to alkynes using copper salts: formation of benzene derivativesJournal of the Chemical Society, Chemical Communications, 1995
- Development of a Titanocene-Catalyzed Enyne Cyclization/Isocyanide Insertion ReactionJournal of the American Chemical Society, 1994
- Cyclocarbonylation of 1,6-Enynes Promoted by Iron CarbonylsOrganometallics, 1994
- Metallacycle Transfer from Zirconium to Main Group Elements: A Versatile Synthesis of HeterocyclesJournal of the American Chemical Society, 1994
- Titanocene-catalyzed conversion of enynes to bicyclic cyclopentenonesJournal of the American Chemical Society, 1993
- Reductive cyclization of ester-containing enynes with a practical titanocene reagent. Synthesis of bicyclic cyclopentenones and iminocyclopentenesThe Journal of Organic Chemistry, 1992
- Regio- and stereocontrolled catalytic palladium- and nickel 'ene-type' cyclizationsPublished by Walter de Gruyter GmbH ,1990
- A Simple Preparation of Cyanosilanes from the Corresponding Chloroderivatives by TranscyanogenationBulletin des Sociétés Chimiques Belges, 1987
- Titanium-mediated synthesis of (E,E)-exocyclic dienes. Application to the preparation of polycyclic compoundsJournal of the American Chemical Society, 1984
- Base-catalysed intramolecular cycloadditions of allyl 3-phenylprop-2-ynyl ethers and 4-methylpent-4-en-2-ynyl prop-2-ynyl ethersJournal of the Chemical Society, Perkin Transactions 1, 1975