This report describes the synthesis of 4-organoselenylisoxazoles via FeCl3/RSeSeR-mediated intramolecular cyclization of allcynone O-methyloximes. The optimized conditions allowed the cyclization to proceed at room tempe...
Building from a previous communication, the reaction of sulfenate anions with chiral N-Boc-protected beta-substituted beta-amino iodides was evaluated as a conceptually different synthetic approach to chiral beta-substit...
The reaction of o-alkynylarenesulfoxide with iodine was investigated in detail, revealing functionalities of the formation of alpha-diketones with sulfenyl, sulfinyl, and sulfonyl. Additives can change the ratio of produ...
Aldehyde-bisulfite adducts dervied from unstable parent aldehydes were reductively alkylated in a direct fashion with a variety of amines. This approach features the use of 2-picoline borane as the reducing agent and a p...
The addition of o-halobenzoic acids to active internal alkynes proceeds efficiently in the presence of CuCl2 as a catalyst to give the corresponding isocoumarin derivatives in moderate to good yields. This strategy offer...
An analysis of the palladium-catalyzed activation of carbon-carbon single bonds within triarylmethanols has led to a greater understanding of factors influencing the beta-aryl elimination process responsible for C-C bond...
The amphimedosides, discovered in 2006, are the first examples of naturally occurring glycosylated alkoxyamines. We report syntheses of amphimedosides A-C that feature a stereoselective oxyamine neoglycosylation and foun...
A new planar and centrally chiral bicyclic 1,2,4-triazolium salt has been synthesized from [2.2]paracyclophane and phenylglycinol. The N-heterocyclic carbene (NHC) copper(I) complex generated in situ by the reaction of t...
The Pd-catalyzed TBHP-mediated Wacker-type oxidation of internal alkenes is reported. The reaction uses 2(4,5-dihydro-2-oxazolyl)quinoline (Quinox) as ligand and TBHP(aq) as oxidant to deliver single ketone constitutiona...
The reaction of propargylic carbonates with 4-hydroxy-2-pyrones in the presence of a palladium catalyst is described. By the choice of the reaction temperature, two types of the substituted furo[3,2-c]pyran-4-one derivat...
An efficient method for the synthesis of 3,5-disubstituted pyrazoles is described. The reactions of 1,3-dialkynes with hydrazine proceeded smoothly in dimethyl sulfoxide under mild reaction conditions to produce 3,5-disu...
We describe an improved synthesis of (-)-5,11-dideoxytetrodotoxin from an enone, which was used for synthesis of tetrodotoxin and its analogues in this laboratory. One of the major modifications was to establish a two-st...