Nickel-Catalyzed Enantioselective Cross-Couplings of Racemic Secondary Electrophiles That Bear an Oxygen Leaving Group
- 1 February 2012
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 134 (6) , 2966-2969
Abstract
To date, effective nickel-catalyzed enantioselective cross-couplings of alkyl electrophiles that bear oxygen leaving groups have been limited to reactions of allylic alcohol derivatives with Grignard reagents. In this Communication, we establish that, in the presence of a nickel/pybox catalyst, a variety of racemic propargylic carbonates are suitable partners for asymmetric couplings with organozinc reagents. The method is compatible with an array of functional groups and utilizes commercially available catalyst components. The development of a versatile nickel-catalyzed enantioselective cross-coupling process for electrophiles that bear a leaving group other than a halide adds a significant new dimension to the scope of these reactions.Keywords
This publication has 25 references indexed in Scilit:
- Catalytic Asymmetric γ-Alkylation of Carbonyl Compounds via Stereoconvergent Suzuki Cross-CouplingsJournal of the American Chemical Society, 2011
- Nickel-Catalyzed Cross-Couplings Involving Carbon−Oxygen BondsChemical Reviews, 2010
- Room-temperature nickel-catalysed cross-couplings of aryl chlorides with arylzincsChemical Communications, 2010
- Asymmetric Alkyl−Alkyl Cross-Couplings of Unactivated Secondary Alkyl Electrophiles: Stereoconvergent Suzuki Reactions of Racemic Acylated HalohydrinsJournal of the American Chemical Society, 2010
- Secondary Alkyl Halides in Transition‐Metal‐Catalyzed Cross‐Coupling ReactionsAngewandte Chemie International Edition, 2009
- Asymmetric Cross‐Coupling of Non‐Activated Secondary Alkyl HalidesAngewandte Chemie International Edition, 2008
- Nickel-Catalyzed Asymmetric Cross-Couplings of Racemic Propargylic Halides with Arylzinc ReagentsJournal of the American Chemical Society, 2008
- Ligand Redox Effects in the Synthesis, Electronic Structure, and Reactivity of an Alkyl−Alkyl Cross-Coupling CatalystJournal of the American Chemical Society, 2006
- Nickel-Catalyzed Cross-Couplings of Organosilicon Reagents with Unactivated Secondary Alkyl BromidesJournal of the American Chemical Society, 2004
- Enantioselective Nickel Catalyzed Grignard Cross Coupling of Allyl Electrophiles. The Influence of the Alkyl Group of the Grignard ReagentOrganometallics, 1994