Copper‐Catalyzed Enantioselective β‐Boration of Acyclic Enones
- 2 February 2009
- journal article
- Published by Wiley in Chemistry – A European Journal
- Vol. 15 (8), 1939-1943
- https://doi.org/10.1002/chem.200802150
Abstract
The enantioselective beta-boration of various acyclic enones has been studied by using chiral diphosphine-copper complexes. Good to excellent yields and enantioselectivities (up to 97 % ee (enantiomeric excess)) were observed for a range of substrates under optimized conditions. In this transformation, the addition of a controlled amount of alcohol, especially methyl alcohol, is critical to obtain products in high ee and yield. This methodology accommodates structural variation of acyclic enones and provides access to a range of functionalized chiral organoboronates in high enantiomeric purity.Keywords
This publication has 21 references indexed in Scilit:
- Copper-Catalyzed Enantioselective Conjugate Addition of Grignard Reagents to Acyclic EnonesJournal of the American Chemical Society, 2004
- Platinum catalysed 3,4- and 1,4-diboration of α,β-unsaturated carbonyl compounds using bis-pinacolatodiboronChemical Communications, 2004
- CuH‐Catalyzed Asymmetric Conjugate Reductions of Acyclic EnonesAngewandte Chemie-International Edition, 2003
- CuH-Catalyzed Asymmetric Conjugate Reductions of Acyclic EnonesAngewandte Chemie, 2003
- Rhodium-Catalyzed Carbon−Carbon Bond Forming Reactions of Organometallic CompoundsChemical Reviews, 2002
- Rhodium-catalyzed 1,4-addition reactions of diboron reagents to electron deficient olefinsTetrahedron Letters, 2002
- Copper‐catalyzed Enantioselective Conjugate Addition Reactions of Organozinc ReagentsPublished by Wiley ,2002
- Addition Reactions of Bis(pinacolato)diborane(4) to Carbonyl Enones and Synthesis of (pinacolato)2BCH2B and (pinacolato)2BCH2CH2B by Insertion and CouplingOrganometallics, 2001
- Boration of an α,β-enone using a diboron promoted by a copper(I)–phosphine mixture catalystTetrahedron Letters, 2000
- Platinum catalysed 1,4-diboration of α,β-unsaturated ketonesChemical Communications, 1997