Recent Advances on the Organocatalyzed Enantioselective α-heterofunctionalization of Carbonyl Compounds

Abstract

Abstract:This review covers literature on organocatalyzed enantioselective α-heterofunctionalization of carbonyl compounds from 2006 to 2009. In this review, we will consider those reactions in which a new carbon-heteroatom bond is formed using a chiral organic molecule as catalyst, excluding those processes, which involve the modification on the hybridization of a previously functionalized carbonyl compound. Using this straightforward synthetic strategy, a wide range of valuable chiral building blocks such as α-amino acids, α-amino alcohols, epoxides, 1,2-diols, α-sulfenylated, α-selenenylated and α-halogenated carbonyl derivatives can be obtained by this simple and advantageous methodology.

Multicomponent Bifunctionalization of Methyl Ketones Enabled by Heterogeneous Catalysis and Solar Photocatalysis in Water

“…Over the past few decades, significant advances have been achieved in developing novel and efficient methods for the synthesis of α-functionalized ketones because such compounds are versatile intermediates for the construction of a variety of natural products, advanced materials, as well as pharmaceuticals and related compounds. , Recently, the direct C­(sp 3 )-H functionalization reactions have been regarded as a promising approach for the α-functionalization of ketones due to their advantages such as atom- and step-economy. Based on this strategy, various solutions to the formation of α-functionalized ketones have been provided, including the iodine-promoted transformation, − transition metal catalysis, − and so on. − For example, Maulide’s group in 2020 reported a triflic anhydride-mediated α-arylation of acetophenones via metal-free electrophilic activation (Scheme a, top) . Later, Nishikata and co-workers developed an efficient copper-organocatalyst system for the C–H alkylation of ketones (Scheme a, middle) .…”