Trivalent boron nucleophile as a new tool in organic synthesis: reactivity and asymmetric induction
- 15 February 2012
- journal article
- review article
- Published by Royal Society of Chemistry (RSC) in Chemical Society Reviews
- Vol. 41 (9) , 3558-3570
Abstract
Boron compounds have been traditionally regarded as “Lewis acids” preferring to accept electrons rather than donate them in the course of their reactions but current examples of unusual reactivity between tricoordinated boranes and electrophilic sites suggest a new conceptual context for the boryl moieties, based on their nucleophilic character which can be enhanced depending on the substituents on boron.Keywords
This publication has 81 references indexed in Scilit:
- Spectroscopic and Structural Characterization of the CyNHC Adduct of B2pin2 in Solution and in the Solid StateThe Journal of Organic Chemistry, 2011
- NHC‐Cu‐Catalyzed Enantioselective Hydroboration of Acyclic and Exocyclic 1,1‐Disubstituted Aryl AlkenesAngewandte Chemie International Edition, 2011
- Transition‐Metal‐Free Diboration Reaction by Activation of Diboron Compounds with Simple Lewis BasesAngewandte Chemie International Edition, 2011
- Enantioselective Synthesis of trans-Aryl- and -Heteroaryl-Substituted Cyclopropylboronates by Copper(I)-Catalyzed Reactions of Allylic Phosphates with a Diboron DerivativeJournal of the American Chemical Society, 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
- Desymmetrization of meso‐2‐Alkene‐1,4‐diol Derivatives through Copper(I)‐Catalyzed Asymmetric Boryl Substitution and Stereoselective Allylation of AldehydesAngewandte Chemie International Edition, 2010
- sp2−sp3 Hybridized Mixed Diboron: Synthesis, Characterization, and Copper-Catalyzed β-Boration of α,β-Unsaturated Conjugated CompoundsOrganic Letters, 2009
- Efficient C−B Bond Formation Promoted by N-Heterocyclic Carbenes: Synthesis of Tertiary and Quaternary B-Substituted Carbons through Metal-Free Catalytic Boron Conjugate Additions to Cyclic and Acyclic α,β-Unsaturated CarbonylsJournal 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