Organoboron Compounds Towards Asymmetric Pericyclic Reaction; Exploitation to Bioactive Molecule Synthesis

Abstract

Organic frameworks containing boron as one of the units have wide application in organic synthesis. Due to the non‐toxicity and cheap accessibility, the organoboron compounds have gained increased demand towards the organic chemist. Besides, there has been a huge progress in the area of chiral organoboron synthesis, which allows direct access to chiral synthons. Among other methods developed for the asymmetric synthesis of organoboron compounds, pericyclic reaction plays an important role. Cycloaddition reactions using vinyl boronic esters have been extensively reported for the synthesis of cyclic boronic esters. Asymmetric cycloaddition using organoboron compound opens a quick access to various intermediates with multiple chiral centers, which has been utilized for the total synthesis of bioactive molecules. This mini‐review outlines various asymmetric pericyclic reactions developed to date demonstrating its applicability towards bioactive molecule synthesis.

Highly Efficient Asymmetric [3+2] Cycloaddition Promoted by Chiral Aziridine-Functionalized Organophosphorus Compounds

“…Within the above methodology, new trends are emerging, including, for example, photocatalysis [2] and asymmetric synthesis using free radicals [3]. Among the very wide variety of asymmetric reactions, stereodifferentiating pericyclic reactions [4], including cycloadditions [5], deserve special mention. Among the products of asymmetric cycloaddition reactions, chiral systems containing a pyrrolidine ring often play a key role in biological and pharmacological research [6].…”

DFT calculations reveal the origin of controllable synthesis of β-boronyl carbonyl compounds from Cu/Pd-cocatalyzed four-component borocarbonylation of vinylarenes

“…[6][7][8][9] Among the methodologies for their preparation, transition metal-catalyzed borofunctionalization of alkenes offers a promising strategy, as it enables the simultaneous installation of distinct functional groups (a carbonyl group and a borane group) across the C-C double bond. [10][11][12][13] Many transition metal complexes, including those of palladium, 14 rhodium, 15 copper, 16 and cobalt, 17 have been found to facilitate this type of transformation.…”

Progress in the Electrochemical Synthesis of Organoboron Compounds

“…Additionally, organoboron species have been used as bio-isosteres [30][31] of carboxylic acids to alter the physicochemical properties of lead candidates in drug discovery. Furthermore, they are used as the versatile building blocks in organic synthesis for molecular transformations, [32][33][34][35] and act as essential reaction partners in Suzuki-Miyaura cross-coupling reactions [36][37] or Chan-Lam reactions. [38] Over the last few years, there has been a growing interest in developing practical and convenient methods for the synthesis of organoboron compounds, either by traditional organic synthesis based on highly reactive organolithium or Grignard reagents with electrophilic boron species, followed by transesterification and hydrolysis [39][40][41][42][43] or photochemical catalysis.…”