Catalytic asymmetric conjugate boration of α,β-unsaturated sulfones
- 16 May 2011
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Chemical Communications
- Vol. 47 (23), 6701-6703
- https://doi.org/10.1039/c1cc11949d
Abstract
The α,β-unsaturated sulfones are suitable activated olefins in catalytic asymmetric conjugate β-boration. These substrates undergo smooth conjugate addition of bis(pinacolato)diboron [B2(pin)2] catalyzed by nonracemic CuI-diphosphine complexes to provide, upon subsequent oxidation, β-hydroxy sulfones in good yields and high enantiocontrol.Keywords
This publication has 37 references indexed in Scilit:
- Stereoconvergent Synthesis of Chiral Allylboronates from an E/Z Mixture of Allylic Aryl Ethers Using a 6-NHC−Cu(I) CatalystJournal of the American Chemical Society, 2011
- Enantioselective Synthesis of (Z)-1,2-anti-2,5-anti-Triol Monosilyl Ethers Using a Cross-Metathesis Allylboration SequenceOrganic Letters, 2010
- Enantioselective Synthesis of Boron-Substituted Quaternary Carbons by NHC−Cu-Catalyzed Boronate Conjugate Additions to Unsaturated Carboxylic Esters, Ketones, or ThioestersJournal of the American Chemical Society, 2010
- Metal‐Free Catalytic Boration at the β‐Position of α,β‐Unsaturated Compounds: A Challenging Asymmetric InductionAngewandte Chemie-International Edition, 2010
- Chiral Boronate Derivatives via Catalytic Enantioselective Conjugate Addition of Grignard Reagents on 3-Boronyl Unsaturated Esters and ThioestersJournal of the American Chemical Society, 2010
- Enantioselective Conjugate BorylationAngewandte Chemie-International Edition, 2010
- Vicinal Diboronates in High Enantiomeric Purity through Tandem Site-Selective NHC−Cu-Catalyzed Boron−Copper Additions to Terminal AlkynesJournal of the American Chemical Society, 2009
- Catalytic Asymmetric Synthesis of Chiral Tertiary Organoboronic Esters through Conjugate Boration of β-Substituted Cyclic EnonesJournal of the American Chemical Society, 2009
- Efficient Boron−Copper Additions to Aryl-Substituted Alkenes Promoted by NHC−Based Catalysts. Enantioselective Cu-Catalyzed Hydroboration ReactionsJournal of the American Chemical Society, 2009
- Copper‐Catalyzed Enantioselective β‐Boration of Acyclic EnonesChemistry – A European Journal, 2009