Copper-Catalyzed Asymmetric Ring Opening of Oxabicyclic Alkenes with Grignard Reagents
- 24 March 2005
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 70 (9) , 3734-3736
- https://doi.org/10.1021/jo050015l
Abstract
[reaction: see text] Simple Grignard reagents were applied in copper-catalyzed asymmetric ring-opening reactions of oxabenzonorbornadiene derivatives using spiro phosphoramidite ligands. Excellent anti-stereoselectivities and good enantioselectivities were achieved.Keywords
This publication has 24 references indexed in Scilit:
- Synthesis of Monodentate Chiral Spiro Phosphonites and the Electronic Effect of Ligand in Asymmetric HydrogenationThe Journal of Organic Chemistry, 2004
- Cationic Planar Chiral Palladium P,S Complexes as Highly Efficient Catalysts in the Enantioselective Ring Opening of Oxa‐ and Azabicyclic AlkenesAngewandte Chemie International Edition in English, 2004
- Scope of Palladium-Catalyzed Alkylative Ring OpeningJournal of the American Chemical Society, 2004
- Highly Enantioselective Copper-Catalyzed Conjugate Addition of Diethylzinc to Enones Using Chiral Spiro Phosphoramidites as LigandsThe Journal of Organic Chemistry, 2003
- 1-Phosphino-2-sulfenylferrocenes: efficient ligands in enantioselective palladium-catalyzed allylic substitutions and ring opening of 7-oxabenzonorbornadienesChemical Communications, 2002
- Palladium-Catalyzed Enantioselective Alkylative Ring OpeningJournal of the American Chemical Society, 2000
- Novel Spiro Phosphinite Ligands and Their Application in Homogeneous Catalytic Hydrogenation ReactionsJournal of the American Chemical Society, 1997
- Using ring-opening reactions of oxabicyclic compounds as a strategy in organic synthesisPublished by Springer Nature ,1997
- Nickel-Catalyzed Addition of Grignard Reagents to Oxabicyclic Compounds. Ring-Opening Reactions with Previously Unreactive Substrates and NucleophilesThe Journal of Organic Chemistry, 1996
- Ring Opening Reactions of Oxabicyclic Compounds as a Route to Cyclic and Acyclic Compounds with Multiple StereocentersSynlett, 1993