Copper‐Catalyzed Enantioselective Markovnikov Protoboration of α‐Olefins Enabled by a Buttressed N‐Heterocyclic Carbene Ligand
- 12 December 2017
- journal article
- research article
- Published by Wiley in Angewandte Chemie International Edition
- Vol. 57 (5) , 1376-1380
Abstract
Reported is a highly enantioselective copper‐catalyzed Markovnikov protoboration of unactivated terminal alkenes. A variety of simple and abundant feedstock α‐olefins bearing a diverse array of functional groups and heterocyclic substituents can be used as substrates, and the reaction proceeds under mild reaction conditions at ambient temperature to provide expedient access to enantioenriched alkylboronic esters in good regioselectivity and with excellent enantiocontrol. Critical to the success of the protocol was the development and application of a novel, sterically hindered N‐heterocyclic carbene, (R,R,R,R)‐ANIPE, as the ligand for copper.Keywords
Funding Information
- National Natural Science Foundation of China (21690074, 21702182)
This publication has 75 references indexed in Scilit:
- Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C–C BondsChemical Reviews, 2015
- Configurationally stable, enantioenriched organometallic nucleophiles in stereospecific Pd-catalyzed cross-coupling reactions: an alternative approach to asymmetric synthesisChemical Science, 2015
- Stereospezifische Kupplungen von sekundären und tertiären BoronsäureesternAngewandte Chemie, 2014
- Stereospecific Couplings of Secondary and Tertiary Boronic EstersAngewandte Chemie International Edition, 2014
- Boronic Acids2011
- Asymmetrische Hydroborierung von 1,1‐disubstituierten AlkenenAngewandte Chemie, 2009
- Asymmetric Hydroboration of 1,1‐Disubstituted AlkenesAngewandte Chemie International Edition, 2009
- The Development of Enantioselective Rhodium‐Catalysed Hydroboration of OlefinsAdvanced Synthesis & Catalysis, 2005
- Catalytic Asymmetric Hydroboration: Recent Advances and Applications in Carbon−Carbon Bond‐Forming ReactionsEuropean Journal of Organic Chemistry, 2003
- The development of a simple general procedure for synthesis of pure enantiomers via chiral organoboranesAccounts of Chemical Research, 1988