The six-pots synthesis of latanoprost has been accomplished with excellent diastereo- and enantioselectivities through an organocatalyst-mediated Michael reaction, a substrate-controlled intramolecular Mukaiyama aldol reaction as key steps.

A highly enantioselective method for the catalytic Mukaiyama aldol reaction of silyl enol ethers with aldehydes in aqueous conditions was developed. The desired aldol products were obtained in excellent yields, diastereo- and enantioselectivities. Structural evidence of the pre-catalyst revealed an unprecedented heptadentate Fe(II) complex with the chiral bipyridine ligand.

We report an efficient Mukaiyama-aldol reaction of tryptanthrin with fluorinated enol silyl ethers, which is carried out in methanol without the use of any catalyst. This method is applied to the total synthesis of the difluoro analogues of the natural product Phaitanthrin B.

A new heterogeneous catalyst, hydrophobic TiO4-deposited mesoporous silica, has been designed for the efficient Mukaiyama-aldol condensation, a water-participating Lewis acid-catalyzed reaction between a hydrophobic carbonyl compound and silyl enol ether. The prepared catalyst suspended in water exhibited high catalytic performance as a reusable catalyst for the reaction without a surfactant.

The conversion of a substituted dioxinone to a pyrone was used in an improved synthesis of the AB spiroketal subunit of the spongistatins. This transformation occurred via a hetero-Diels-Alder reaction of an acyl ketene with butyl vinyl ether. A double diastereoselective Mukaiyama aldol reaction is used to provide the hetero-Diels-Alder precursor.

Luminescence-decay measurements in combination with high-performance liquid chromatography analyses were used to study the relationship between rates of catalysis and water-coordination numbers of europium-based precatalysts in the aqueous Mukaiyama aldol reaction. A correlation between reactivity and water-coordination number was observed and is reported here.

Nannocystin A is a 21-membered cyclodepsipeptide showing remarkable anticancer properties. Described is the total synthesis of nannocystin A, which features an asymmetric vinylogous Mukaiyama aldol reaction for efficient assembly of the penultimate open-chain precursor and a pivotal intramolecular Heck cross-coupling for the final macrocyclization.

A slight excess of silyl trifluoromethanesulfonate mediates a tandem enol silane formation-Mukaiyama aldol reaction in the presence of Hunig’s base. Preformation of the enol silane is unnecessary for efficient reactions, which proceed in 75-97% yield for the addition of aryl methyl ketones and acetate esters to non-enolizable aldehydes. Mechanistic data suggests that free amine is crucial for f...