Catalytic methodologies for the β-boration of conjugated electron deficient alkenes

Abstract

The area of boron conjugate addition via diboration (β-boration) has grown rapidly since the first examples appeared in the late 1990s. This article aims to give a comprehensive review of the current advances in β-boration (of electron deficient alkenes), providing a commentary upon the development of the asymmetric version. To date, many mechanistic models have been put forward to explain the experimental observations and this review surveys some of these key ideas. Recently, the development of organocatalytic methodologies that facilitate β-boration have also been demonstrated and current ideas regarding the mechanisms of such processes are examined.

Enantioselective 1,1-Arylborylation of Alkenes: Merging Chiral Anion Phase Transfer with Pd Catalysis

“…1 Accordingly, there has been significant interest in developing new enantioselective methods that afford these motifs. Examples of catalytic enantioselective hydroboration, 2 allylic borylation, 3 conjugate borylation, 4 reductive transformations of vinyl boronates 5 and 1,2-diborylation of aromatic imines and styrenes have been reported. 6 Furthermore, several enantioselective borylation reactions utilizing stoichiometric amounts of chiral auxiliaries have been disclosed.…”

Singular Metal Activation of Diboron Compounds

“…[155][156][157][158][159][160][161][162][163][164][165] The mode of activation depends on the nature of the diboron compound and the inherent Lewis acid properties. From tetrahalide diboron compounds to tetra(alkoxy)diboron compounds, the reactivity diminishes significantly at the same time that stability of the resulting organoboron compounds increases.…”

An Efficient and Waste-Minimized One-Pot Procedure for the Preparation of N-Boc-γ-amino Alcohols Starting from α,β-Unsaturated Ketones in Flow

“…11 A large number of target molecules, including β-amino acids, γ-amino alcohols, pharmaceuticals and natural products, 12 have been synthesized starting from β-amino carbonyl compounds. 13 These versatile intermediates can be prepared by the conjugate addition of a Nnucleophile (e.g.…”