Reiko Yanada

Indium(III)-Catalyzed Tandem Reaction with Alkynylbenzaldehydes and Alkynylanilines to Heteroaromatic Compounds

Starting from ortho-alkynylbenzaldehydes and ortho-alkynylanilines, In(OTf)3-catalyzed synthesis of ring-condensed heteroaromatic compounds was developed via a domino intramolecular nucleophilic attack/intermolecular cycloaddition/dehydration reaction.

Cleavage of Carbon–Carbon Triple Bond: Direct Transformation of Alkynes to Nitriles

A new cleavage reaction of carbon-carbon triple bonds proceeds efficiently with NIS and TMSN3, giving the corresponding nitriles in moderate to good yields.

Concise total synthesis of calothrixins A and B.

The concise total synthesis of calothrixins A and B has been accomplished by utilizing the one-pot formation of hexatriene as a key intermediate via the palladium-catalyzed tandem cyclization/cross-coupling reaction of triethyl(indol-2-yl)borate. In another key transformation, the indolo[3,2-j]phenanthridine core was prepared in high yield via Cu(I)-mediated 6π-electrocyclization.

Regio- and stereoselective multisubstituted enol ester synthesis.

Regio- and stereoselective cohalogenation of alkynes with NXS (X = Br, I) was achieved, and the stereoselectivity of the resulting alkenes was dependent on the substituent on the alkyne. Cohalogenation and successive cross-coupling gave multisubstituted enol esters in a one-pot process.

Multisubstituted Furan Formation from (Z)- or (E)-Enynyl Acetates: Tandem Reactions Accelerated by Electron-Donating Groups on Aromatic Rings

Multisubstituted furans were readily prepared from (Z)- or (E)-conjugated enynyl acetates with NXS under metal-free conditions at room temperature via the same haloallenyl ketone intermediates. This tandem haloallenyl ketone formation-furan formation reaction sequence was accelerated by electron-donating groups on the aromatic rings.

Grignard reaction 0f 2-phenyl-tetrahydropyrrolo-1,5,2-oxazaphospholes, observation of the stereospecific inversion of configuration

Abstract Grignard reaction of bicyclic oxazaphospholes proceeded with inversion of configuration to provide chiral phosphinic esters of known absolute configurations.

One-pot approach to 2,3-disubstituted-2,3-dihydro-4-quinolones from 2-alkynylbenzamides.

Concise and efficient syntheses of various trans-2,3-disubstituted-2,3-dihydro-4-quinolones have been achieved via tandem Hofmann-type rearrangement of 2-alkynylbenzamides, nucleophilic addition of alcohols to the isocyanate intermediates, intermolecular [2+2]-cycloaddition with carbon-carbon triple bonds and aldehydes, and intramolecular aminocyclization of nitrogen of carbamates to the α,β-unsaturated ketones.

Stereochemistry of the base-catalyzed methanolysis of 2-phenyl-tetrahydropyrrolo-1,3,2-oxazaphospholes

Abstract Diastereomerically pure bicyclic oxazaphospholes were prepared from L-prolinol and phenylphosphonic or thiophosphonic dichloride and their absolute configurations were determined based on the interpretation of NMR spectra. The base-catalyzed methanolysis of those compounds was found to proceed by exclusive PO bond cleavage with complete inversion of configuration.

Investigation of the regioselectivity on the reaction of 2-indolylcyanocuprate with N-(prop-2-en-1-ylidene)-aminium chloride derivatives

Regioselectivity on the reaction of (1-methylindol-2-yl)cyanocuprate with N-(prop-2-en-1-ylidene)aminium chlorides was investigated.

Regioselective Reaction of 2-Indolylcyanocuprates with Electrophiles

The reaction of 2-indolylcyanocuprate with electrophiles was found to give rise to 2- and 3-substituted indoles in regioselective manner.