Catalytic Asymmetric Methallylation of Ketones with an (H8-BINOLate)Ti-Based Catalyst
- 1 September 2006
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 8 (20) , 4413-4416
- https://doi.org/10.1021/ol061417y
Abstract
The first catalytic asymmetric methallylation of ketones is reported. The catalyst, which is generated from titanium tetraisopropoxide, H8-BINOL, 2-propanol, and tetramethallylstannane, reacts with ketones in acetonitrile to afford tertiary homoallylic alcohols in fair to excellent yields (55−99%) and fair to high enantioselectivities (46−90%). Ozonolysis of the resulting products provides access to chiral β-hydroxy ketones, which are not readily prepared from direct asymmetric aldol reaction of acetone with ketones.Keywords
This publication has 25 references indexed in Scilit:
- Silver-Catalyzed Asymmetric Sakurai−Hosomi Allylation of KetonesJournal of the American Chemical Society, 2005
- Catalytic Asymmetric Allylation of Ketones and a Tandem Asymmetric Allylation/Diastereoselective Epoxidation of Cyclic EnonesJournal of the American Chemical Society, 2004
- Catalytic Asymmetric Vinylation of KetonesJournal of the American Chemical Society, 2004
- On the use of mixtures of organotin species for catalytic enantioselective ketone allylation—a detective storyOrganic & Biomolecular Chemistry, 2004
- Excited‐State Deprotonation and H/D Exchange of an Iridium Hydride ComplexAngewandte Chemie International Edition in English, 2003
- Multicenter Strategy for the Development of Catalytic Enantioselective Nucleophilic Alkylation of Ketones: Me2Zn Addition to α‐KetoestersAngewandte Chemie International Edition in English, 2003
- Enantioselective Alkynylation of Aromatic Ketones Catalyzed by Chiral Camphorsulfonamide LigandsAngewandte Chemie International Edition in English, 2003
- Asymmetric Addition of Alkylzinc Reagents to Cyclic α,β-Unsaturated Ketones and a Tandem Enantioselective Addition/Diastereoselective Epoxidation with DioxygenJournal of the American Chemical Society, 2003
- Catalytic Enantioselective Addition of Allylic Organometallic Reagents to Aldehydes and KetonesChemical Reviews, 2003
- A Catalytic Enantioselective Route to Hydroxy-Substituted Quaternary Carbon Centers: Resolution of Tertiary Aldols with a Catalytic AntibodyJournal of the American Chemical Society, 1999