Mikio Kawada

Stereocontrolled formation of cis and trans ring junctions in hydrindane and decalin systems by palladium-catalyzed regioselective and stereospecific hydrogenolysis of allylic formates

Both cis and trans ring junctions can be generated selectively in hydrindane, decalin, and-steroid systems by the palladium-catalyzed regioselective and stereospecific hydrogenolysis of allylic formates

Synthetic application of phenylthio- and phenylsulfonylmethyl ethers to aldehydes, methylals, carboxylic acids, and enol or dienol ethers

Abstract Novel synthetic application of the title compounds to aldehydes, methylals, carboxylic acids, and enol or dienol ethers has been newly developed.

Highly stereoselective synthesis of (2E,4E)-dienamides and (2E,4E)-dienoates via a double elimination reaction

Abstract Highly stereoselective synthesis of (2E,4E)-dienamides and (2E,4E)-dienoates was achieved through a double elimination reaction of β-acetoxy sulfones.

Palladium-catalyzed reactions of 2-alkynyl carbonates with olefins. A new synthetic method for vinyl allenes.

Abstract Palladium-catalyzed reaction of 2-alkynyl carbonates (propargylic carbonates) with olefins proceeds smoothly in the presence of triethylamine and potassium bromide to give vinyl allenes (1,2,4-trienes) in good yields.

Synthesis of α-vinylidene-β-lactams by the palladium-catalyzed carbonylation of 4-amino-2-alkynyl carbonates

Abstract The palladium-catallyzed carbonylation of 4-amino-2-alkynyl carbonates proceeded under mild conditions to afford α-vinylidene-β-lactams in moderate yields. The cyclic phosphite, 4-ethyl-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane was found to be the best ligand.

A new synthetic method for α-ketosilanes employing methoxy(phenylthio)trialkylsilylmethane as an α-silylacyl anion equivalent

Abstract Development of a new synthetic method for α-ketosilanes can be achieved by a sequence of alkylation of methoxy(phenylthio)trialkylsilylmethane and oxidation with NaIO 4 .

Preparation of 4-hydroxy-2-alkenenitriles from phrnylsulfinylacetonitrile with keetones or aldehydes, and its synthetic application to substituted furans

Abstract The reaction of phenylsulfinylacetonitrile 1 with ketones or aldehydes gave 4-hydroxy-2-alkenenitriles which were converted to 2- and/or 3-substituted furans by the treatment with diisobutylaluminumhydride(DIBAL) followed by acid hydrolysis.

Palladium-catalyzed rearrangement of α-cyanoallylic acetates application to a new synthetic method for furans

Abstract Various types of α-cyanoallylic acetates were undergone the palladium-catalyzed rearrangement to give the γ-acetoxy-α,β-unsaturated nitriles in high yields. These rearranged acetates were conveniently transformed into the furan derivatives often encountered in natural products by the reduction using diisobutylaluminum hydride.

Stereocontrolled formation of cis and trans ring junctions in hydrindane, decalin, and steroid systems by palladium-catalyzed regioselective and stereospecific hydrogenolysis of allylic formates

Abstract Both the cis and trans ring junctions can be generated selectively in hydrindane, decalin and steroid systems by the palladium-catalyzed regioselective and stereospecific decarboxylation-hydrogenolysis of allylic formates. The trans junctions were formed from 3β allylic formates of decalin and steroid and 5β allylic formates of hydrindane. The corresponding 3α and 5α formates generate the cis ring junction.

Palladium-catalyzed tandem carbonylation and intramolecular diels-alder reaction of 4-alken-2-ynyl carbonates: a new synthetic method for polycyclic compounds

A new synthetic method for polycyclic compounds via the palladium-catalyzed tandem carbonylation and intramolecular Diels-Alder reaction is described.