Cyclization into Hydrindanones Using Samarium Diiodide
- 25 April 2000
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 65 (10) , 3099-3106
- https://doi.org/10.1021/jo9918450
Abstract
Samarium(II) iodide has been employed to promote vinylogous pinacol coupling reaction of aldehyde onto alpha,beta-unsaturated ketones. The diastereoselectivity of 6-endo products was changed by addition of a proton source and/or HMPA and by the reaction temperature. The cyclization reactions described herein provide a general approach to the syntheses of 3,3-dimethylhydrindanes with a cis-relationship between the OH at C-4 and the proton at C-3a with good diastereoselectivity and under mild reaction conditions.Keywords
This publication has 29 references indexed in Scilit:
- Diverse Methods for Medium Ring SynthesisAccounts of Chemical Research, 1998
- Structure of conocephalenol, a sesquiterpenoid alcohol from the European liverwort Conocephalum conicum: determination of the absolute configuration by total synthesisJournal of the Chemical Society, Perkin Transactions 1, 1995
- Total Synthesis of (-)-Grayanotoxin IIIThe Journal of Organic Chemistry, 1994
- Stereoselective Cyclization Mediated by Samarium(II) Iodide Using Allyl Sulfides and Sulfones as Ketyl Radical AcceptorsThe Journal of Organic Chemistry, 1994
- Stereoselective Formation oftrans-Decalin andcis-Decalin Skeletons via Hydroxy Group Directed Cyclization Induced by Samarium(II) IodideSynlett, 1993
- Application of lanthanide reagents in organic synthesisChemical Reviews, 1992
- Synthesis and relative structure of conocephalenol, a sesquiterpene alcohol isolated from the european liverwort Conocephalum conicumJournal of the Chemical Society, Perkin Transactions 1, 1991
- Absolute configurations of the liverwort sesquiterpenoids, (–)-chiloscyphone and (+)-chiloscypholone: total synthesis of optically active compoundsJournal of the Chemical Society, Perkin Transactions 1, 1989
- Intramolecular reductive cyclization of unsaturated keto- or aldo-esters by samarium(II) di-iodide: a ready synthesis of bicyclic γ-lactonesJournal of the Chemical Society, Chemical Communications, 1987
- Lanthanides in organic synthesis. 3. A general procedure for five- and six-membered ring annulationThe Journal of Organic Chemistry, 1986