Diastereoselectivity in the Reduction of α-Oxy- and α-Amino-Substituted Acyclic Ketones by Polymethylhydrosiloxane
- 6 December 2002
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 68 (2) , 594-596
- https://doi.org/10.1021/jo0260544
Abstract
Diastereoselectivity in the reduction of α-alkoxy-, α-acyloxy-, and α-alkylamino-substituted ketones with polymethylhydrosiloxane (PMHS) in the presence of fluoride ion catalysis was investigated. High syn-selectivity was observed in the reduction of α-alkoxy, α-acyloxy, and α-dialkylamino ketones. Reduction of α-monoalkylamino ketone proceeded in anti-selective manner with moderate selectivity. The observed selectivity is explained based on Felkin-Anh and Cram-chelate models.Keywords
This publication has 14 references indexed in Scilit:
- Regio- and stereo-selectivities in some nucleophilic reactionsPublished by Springer Nature ,2006
- Around and beyond Cram's RuleChemical Reviews, 1999
- The asymmetric reduction of ketones using chiral ammonium fluoride salts and silanesTetrahedron Letters, 1997
- Syn/anti diastereoselectivity in the reduction of .alpha.-alkoxy ketones by tin hydride reagentsThe Journal of Organic Chemistry, 1992
- Fluoride ion-catalyzed reduction of aldehydes and ketones with hydrosilanes. Synthetic and mechanistic aspects and an application to the threo-directed reduction of .alpha.-substituted alkanonesThe Journal of Organic Chemistry, 1988
- Zum sterischen Verlauf asymmetrischer Induktionen. II. Beziehungen zwischen Substituenteneinfluß und Reaktionsbedingungen bei der Reduktion racemischer α‐(Phenylalkylamino)‐propiophenone mit verschiedenen KryptobasenJournal für Praktische Chemie, 1973
- Stereochemical Studies. XI. Changes in the Stereochemical Courseof 1, 2-Asymmetric Induction in the Reduction of N-Substituted 2-Aminopropiophenone Derivatives with Sodium BorohydrideCHEMICAL & PHARMACEUTICAL BULLETIN, 1972
- Torsional strain involving partial bonds. The stereochemistry of the lithium aluminium hydride reduction of some simple open-chain ketonesTetrahedron Letters, 1968
- Effects of neighboring functional groups on 1,2-asymmetric induction in the reduction of ketones with sodium borohydrideTetrahedron Letters, 1967
- Studies in Stereochemistry. XXXII. Models for 1,2-Asymmetric InductionJournal of the American Chemical Society, 1963