Solvent-Dependent Diastereoselectivities in Reductions of β-Hydroxyketones by SmI2
- 10 July 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 6 (16) , 2685-2688
- https://doi.org/10.1021/ol049129u
Abstract
The reductions of a series of β-hydroxyketones by SmI2 were examined in THF, DME, and CH3CN using methanol as a proton source. Reductions in THF and DME typically lead to the syn diastereomer with DME providing higher diastereoselectivities. Reductions in CH3CN provided the anti diastereomer predominantly. This study reveals that solvation plays an important role in substrate reduction by SmI2.Keywords
This publication has 11 references indexed in Scilit:
- The Role of Proton Donors in SmI2-Mediated Ketone Reduction: New Mechanistic InsightsJournal of the American Chemical Society, 2003
- Switching between Novel Samarium(II)-Mediated Cyclizations by a Simple Change in Alcohol CosolventOrganic Letters, 2003
- The Remarkable Effect of Cosolvent on a Samarium(II)-Mediated 4-exo-trig Cyclization: Further Synthetic Studies on Pestalotiopsin AThe Journal of Organic Chemistry, 2003
- Aggregation state and reducing power of the samarium diiodide–DMPU complex in acetonitrileTetrahedron Letters, 2000
- On the reduction of tertiary radicals by samarium diiodide (SmI2)Canadian Journal of Chemistry, 2000
- Structure and Energetics of the Samarium Diiodide−HMPA Complex in TetrahydrofuranThe Journal of Organic Chemistry, 1999
- Preparation and reactions of samarium diiodide in nitrilesTetrahedron, 1996
- Sequencing Reactions with Samarium(II) IodideChemical Reviews, 1996
- Coordination chemistry of samarium(II). X-ray crystal structures of SmI2(NCCMe3)2 and SmI2[O(CH2CH2OMe)2]2. The first example of a bent M-N.tplbond.C structureInorganic Chemistry, 1985
- Divalent lanthanide derivatives in organic synthesis. 1. Mild preparation of samarium iodide and ytterbium iodide and their use as reducing or coupling agentsJournal of the American Chemical Society, 1980