Total Synthesis of Citreochlorol Monochloro Analogs via a Catalytically Enantioselective Carbonyl Allylation

An efficient synthetic route to citreochlorol analogs, halogenated polyketide secondary metabolites, is described. The key features are Krische's enantioselective carbonyl allylation, IBr-promoted cyclization, and regioselective epoxide opening. The importance of the route lies in the access of the versatile epoxy ether 14, which opens access to the citreochlorol monochloro derivatives 5 and 6.

Easy access to secondary and tertiary alcohols via metal-free and light mediated radical carbonyl allylation

An organo-photocatalyst catalyzed allylation of aryl ketones and aldehydes using readily available unactivated allylic substrates has been reported.

Nickel-Catalyzed Reductive Allylation of Aldehydes with Allyl Acetates

Carbonyl allylation reactions constitute an important step in the formation of carbon–carbon reactions, and involve various related reactions that chiefly use allylmetal reagents. This report presents a nickel-catalyzed carbonyl allylation reaction using allyl acetate, which produces homoallyl alcohols in moderate to good yields, as an efficient methodology under reductive coupling conditions.

Palladium-Catalyzed Carbonyl Allylation Reactions Using Tin Chloride: A Mini-Review

The treatment of allylic alcohols as synthons of carbanions for carbonyl allylation reactions in the presence of a Pd-SnCl2 system has been one of the most interesting and most useful developments demonstrated by Yoshiro Masuyama and co-workers in the field of organic synthesis. The reaction makes use of palladium as an effective catalyst and tin (II) chloride as a low-valent reducing agent which also effectively transforms the allylic group to a nucleophilic group. The organic, as well as organometallic, chemistry of how the transformations occur and how the metals take part in the reaction is of great interest. These could help allow for better optimization of reagents and solvents, for better control of the extent of reaction or yield of desired product, and for possible applications in other reaction systems. This review will focus primarily on the work of Yoshiro Masuyama and various co-workers on carbonyl allylation reactions making use of a Pd-SnCl2 system or substitutes thereof.