Abstract
α-Functionalization of carbonyl compounds in organic synthesis has traditionally been accomplished via classical enolate chemistry. As α-functionalized carbonyl moieties are ubiquitous in biologically and pharmaceutically valuable molecules, catalytic α-alkylations have been extensively studied, yielding a plethora of practical and efficient methodologies. Moreover, stereoselective carbon–carbon bond formation at the α-position of achiral carbonyl compounds has been achieved by using various transition metal–chiral ligand complexes. This review describes recent advances—in the last 20 years and especially focusing on the last 10 years—in transition metal-catalyzed α-alkylations of carbonyl compounds, such as aldehydes, ketones, imines, esters, and amides and in efficient carbon–carbon bond formations. Active catalytic species and ligand design are discussed, and mechanistic insights are presented. In addition, recently developed photo-redox catalytic systems for α-alkylations are described as a versatile synthetic tool for the synthesis of chiral carbonyl-bearing molecules.
Highlights
To date, a myriad of studies on the effective α-functionalization of carbonyl compounds have been reported [1,2,3]
Primary alcohols 86 were employed as coupling partners for α-alkylation, and this methodology was performed under milder conditions, compared to those of previous transition metal-catalyzed α-functionalizations of unactivated amides or esters, and it exhibited good functional group tolerance
This review summarizes recent transition metal-catalyzed α-alkylation reactions of various carbonyl derivatives
Summary
A myriad of studies on the effective α-functionalization of carbonyl compounds have been reported [1,2,3]. The development of efficient synthetic procedures for the α-functionalization of carbonyls can be daunting Transition metals have their intrinsic disadvantages, such as high cost and toxicity [10]. Transition metal-catalyzed α-alkylation of advantages, such as mild reaction conditions and diverse scope of carbonyl derivatives. C–C coupling via reductive elimination.catalytic palladium-based catalytic reported for such carbonyl α-alkylations and arylations to date [13]. In addition these advancements, systems have been extensively reported for such carbonyl α-alkylations and to arylations to date [13].
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