Issue 43, 2015

Synthesis and application of a dual chiral [2.2]paracyclophane-based N-heterocyclic carbene in enantioselective β-boration of acyclic enones

Abstract

An enantioselective conjugate addition of boron to α,β-unsaturated ketones catalysed by either a N-heterocyclic carbene or a copper–carbene complex generated in situ from a new chiral bicyclic triazolium based on [2.2]paracyclophane is presented. The dual chiral carbene–copper catalyst has significant advantages over its carbene counterpart as an organocatalyst in asymmetric β-boration of acyclic enones, giving a variety of chiral β-boryl ketones in good yields and enantioselectivities. This is a successful example of employing the same N-heterocyclic carbene in one catalytic reaction as both an organocatalyst and a ligand for transition metal catalysis.

Graphical abstract: Synthesis and application of a dual chiral [2.2]paracyclophane-based N-heterocyclic carbene in enantioselective β-boration of acyclic enones

Supplementary files

Article information

Article type
Paper
Submitted
01 Aug 2015
Accepted
01 Sep 2015
First published
01 Sep 2015

Org. Biomol. Chem., 2015,13, 10691-10698

Author version available

Synthesis and application of a dual chiral [2.2]paracyclophane-based N-heterocyclic carbene in enantioselective β-boration of acyclic enones

L. Wang, Z. Chen, M. Ma, W. Duan, C. Song and Y. Ma, Org. Biomol. Chem., 2015, 13, 10691 DOI: 10.1039/C5OB01609F

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