A highly regio- and stereo-selective synthesis of cyclic β-D-glucosides 3 via Pd(0)-catalyzed coupling cyclization of allenyl β-D-glucoside 1 and organic iodides in 20-38% yields is reported. After the deacetylation of 3, we obtained cyclic β-D-glucoses 4 in 90-97% yields, which may have SGLT2 inhibition activities.

It was observed that a PhSiH2I-mediated protocol using PhSiH3 and cat. I2 caused the deiodination of 2-(iodomethyl)-2-phenyltetrahydrofuran. Stemming from the investigation of the mechanism, we found that the PhSiH3-I2 system selectively promotes diverse cascade transformations from cyclic ethers to acyclic alkyl iodides, and the PhSiH3-N-iodosuccinimide (NIS) system also promotes cascade trans...

[reaction: see text] The diastereoselective alkylation of glycolate oxazolidinones has been demonstrated as a method for the enantioselective preparation of alpha-alkoxy carboxylic acid derivatives and selectively protected 1,2-diols. Various protecting groups on the glycolate hydroxyl and multiple substitution patterns on allylic iodides are tolerated in the alkylation. Yields for the alkylati...

We report the Cu-promoted oxidative cross-coupling of αfluoromalonate half-esters and aryl boron reagents to deliver monofluoro α-aryl acetates under mild conditions (in air at room temperature). The reaction uses a simple, readily available monofluorinated building block to generate arylated compounds with functional groups that are not easily tolerated by existing methods, such as aryl bromid...

An asymmetric Ni-catalyzed reductive cross-coupling of (hetero)aryl iodides and benzylic chlorides has been developed to prepare enantioenriched 1,1-diarylalkanes. As part of these studies, a new chiral bioxazoline ligand, 4-heptyl-BiOX (L1), was developed in order to obtain products in synthetically useful yield and enantioselectivity. The reaction tolerates a variety of heterocyclic coupling ...

It has been shown by a number of observers that the administration of iodides both to dogs and to human beings causes an increase in the output of nitrogen in the urine. One of the earliest observers (1) working with dogs showed that this was in part at the expense of the nitrogen excreted in the feces, but that the total amount of nitrogen excreted was none the less increased. We have been abl...