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Kinetics on the cheletropic addition of sulfur dioxide to (E)-1-methoxybutadiene (1) to give the corresponding sulfolene 2 (2-methoxy-2,5-dihydrothiophene-1,1-dioxide) gave the rate law d[2]/dt = k[1] SO2 with x = 2.6 +/- 0.2 at 198 K. Under these conditions, no sultine 3 [(2RS,6RS)-6-methoxy-3,6-dihydro-1,2-oxathiin-2-oxide] resulting from a hetero-Diels-Alder addition was observed, and the cheletropic elimination 2 --> 1 + SO2 did not occur. Ab initio and DFT quantum calculations confirmed that the c

The reactivity of sulfur dioxide toward variously substituted butadienes was explored in an effort to define the factors affecting the competition between the hetero-Diels-Alder and cheletropic additions. At low temperature (< -70degrees), 1-alkyl-substituted 1,3-dienes 1 that can adopt s-cis-conformations add to SO2 in the hetero-Diels-Alder mode in the presence of CF3COOH as promoter. In the case of (E)-1-ethylidene-2-methylidenecyclohexane ((E)-4a), the [4 + 2] cycloaddition of SO2 is fast at -90degrees

The long-standing mystery surrounding the peculiar electronic structure of norbornene and its derivatives is revealed by the direct comparisons of their properties with those of reference analogues with localized double bonds (i.e. Lewis structures). Our b ...

alpha-D-Galactosyl)phenylmethane (1). (alpha- and beta-D-galactosyl)-(difluoro)phenylmethane (2 and 3) have been prepared and their conformations in solution were described by using a combination of force-field calculations and NMR spectroscopic studies. G ...

An efficient and concise total synthesis of (+)-lentiginosine (1) starting from an L-tartaric acid-derived nitrone using organometallic addition, indium-catalyzed reduction, and ring-closing metathesis reaction as the key steps is reported. Structural anal ...

The ketonitrone 8 was prepared from D-fructose as an inexpensive starting material, and was used in a stereoselective synthesis of 1-deoxymannojirimycin (4), its previously unknown N-hydroxy analogue 15, as well as the polyhydroxylated ketonitrone 14. The ...

At low temperature 1-alkoxy-1,3-dienes add to sulfur dioxide activated by a Lewis or Bronstedt acid and generate zwitterionic intermediates that can be quenched by enoxysilanes. The resulting beta,gamma -unsaturated silyl sulfinates can be desilylated and reacted with methyl iodide to provide polyfunctional sulfones. Exploratory studies of this four-component synthesis of sulfones are reported. Enantiomerically pure derivatives containing up to three new stereogenic centers can be obtained using enantiomeri

An interactive computer graphics equipment is used as an output device for representing the results of quantum chemical calculations. The advantages of such displays are illustrated by the description of several applications: (i) interactive visualization of molecular properties and (ii) dynamic representation of unimolecular rearrangements. Several examples are chosen among the latter group of applications: reversible formation of cyclobutene from 1,3-butadiene, intramolecular migration of a methyl group o

The Garcia-Gonzalez reaction Of D-glucose and ethyl acetoacetate generated ethyl 5-[(1'S)-D-erythrosyl]-2-methyl-3-furoate (5), which was converted to ethyl 5-[(1'R)-1',4'-dideoxy-1',4'-imino-D-erythrosyl]-2-methyl-3-furoate (3c) and to ethyl 5-[(1'S)-1',4'-dideoxy-1',4'-imino-D-erythrosyl]-2-methyl-3-furoate (4c). Similar methods were developed to generate other carboxylic acid derivatives such as methyl (see 3e and 4e), isopropyl (see 3f), and butyl esters (see 3g), S-phenyl (see 3a) and S-ethyl thioester

Pancreatic ductal adenocarcinoma (PDAC) is one of the most lethal diseases for which chemotherapy has not been very successful yet. FK866 ((E)-N-(4-(1-benzoylpiperidin-4-yl)butyl)-3-(pyridin-3-yl)acrylamide) is a well-known NAMPT (nicotinamide phosphoribos ...

2-Methylprop-2-ene-1-sulfonyl fluorides can be easily prepared via the ene reaction of methallylsilanes and SO2. In the presence of a base, aldehydes and 2-methylprop-2-ene-1-sulfonyl fluorides give 1.3-(E) and (Z)-dienes. Their (Z) --> (E) isomerization b ...

Efficient methods for the stereoselective synthesis of polyfunctional (E)- and (2)-alkenes and conjugated (EE)- and (E,2)-dienones are presented. They rely upon one-pot, four-component processes that condense 1-oxy-1,3-dienes, silyl enol ethers, SO2, and c ...

Anomalous variations of one-bond C-C scalar coupling constants are observed in going from trinorbornane-to trinorbornene-like structures. Most notably, a IO-Hz increase is observed in the coupling constant involving the C-atoms of the ethano branch facing the C=C bond. An effect of about half the size is characteristic of higher homologues (bicyclo[2.2.2]octenes), but no such effect is observed for monocyclic molecules.

The title compound 4a, a purple transient whose main UV-vis absorption band occurs near 490 nm (epsilon = 5000 M-1 cm-1), has been generated by irradiation of 2,3,5,6-tetramethylene-7-oxonorbornane (5a). It has been observed directly by immobilization in frozen matrices or in polymer films and by time-resolved spectroscopy following nanosecond later flash photolysis of the ketone precursor 5a. Although the matrix-immobilized irradiated samples containing biradical 4a show a triplet electron spin resonance (

New substituted pyrrolidine-3,4-diol derivatives were prepared from D-(-)- and L-(+)-phenyl glycinol. The influence of the configuration and the substitution of the lateral side chain of these derivatives on the inhibition of 25 commercial glycosidases wer ...

At low temperature and in the presence of an acid catalyst, sulfur dioxide undergoes hetero-Diels-Alder additions with 1-oxy-1,3-dienes, giving unstable sultines, which are ionized into zwitterionic species and react as 1-oxyallylic cation intermediates (U ...

Indoleamine 2,3-dioxygenase 1 (IDO1) is an important therapeutic target treatment of diseases such as cancer that involve pathological immune escape. Starting from the scaffold of our previously discovered IDO1 inhibitor 4-phenyl-1,2,3-triazole, we used co ...

Nitrogen-in-the-ring analogues of L-fucose and L-rhamnose were prepared, which feature a spirocyclopropyl moiety in place of the methyl group of the natural sugar. The synthetic route involved a titanium-mediated aminocyclopropanation of a glycononitrile a ...

Zinc iodide‐catalyzed cycloaddition of furan to 1‐cyanovinyl (1′S)‐camphanate or 1‐cyanovinyl (1′R)‐camphanate led to optically pure (1R,2S,4R)‐2‐exo‐cyano‐7‐oxabicyclo[2.2.1]‐hept‐5‐en‐2‐yl (1S')‐camphanate and (1S,2R,4S)‐2‐exo‐cyano‐7‐oxabicyclo[2.2.1]hept‐5‐en‐2‐yl (1R')‐camphanate, respectively. Saponification afforded (1R,4R)‐ and (1S,4S)‐7‐oxabicyclo[2.2.1]‐hept‐5‐en‐2‐one, respectively, and allowing recovery of the chiral auxiliaries (1S)‐ and (1R)‐camphanic acid, respectively. The 7‐oxabicyclo[2.2.1

Alcohols, phenols and carboxylic acids are silylated with very good yields in the presence of silyl methallylsulfinates under non- basic conditions and with the formation of volatile co-products. ...

Pierre Vogel

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Ab initio and experimental studies on the hetero-Diels-Alder and cheletropic additions of sulfur dioxide to (E)-1-methoxybutadiene: A mechanism involving three molecules of SO2

Substituent effect on the competition between hetero-Diels-Alder and cheletropic additions of sulfur dioxide to 1-substituted buta-1,3-dienes

The norbornene mystery revealed

Synthesis and Conformational Analysis of (alpha-D-Galactosyl)phenylmethane and alpha-,beta-Difluoromethane Analogues: Interactions with the Plant Lectin Viscumin

New concise total synthesis of (+)-lentiginosine and some structural analogues

A Short and Convenient Synthesis of 1-Deoxymannojirimycin (DMJ) and N-oxy-Analogues from D-Fructose

Development of a new carbon-carbon bond forming reaction. New organic chemistry of sulfur dioxide. Asymmetric four-component synthesis of polyfunctional sulfones

Dynamic Representation of Quantum Chemical Results Using Computer-Graphics - Molecular-Rearrangements, Art or Science

Synthesis and glycosidase inhibitory activities of 5-(1 ',4 '-dideoxy-1 ',4 '-imino-D-erythrosyl)-2-methyl-3-furoic acid (=5-[3S, 4R)-3,4-dihydroxypyrrolidin-2-yl]-2-methylfuran-3-carboxylic acid) derivitives: New leads as selective alpha-L-fucosidase and beta-galactosidase inhibitors

Identification of new FK866 analogues with potent anticancer activity against pancreatic cancer

One-pot synthesis of 1-aryl-3-methyl-1,3-dienes using methallyl(trimethyl)silane and aldehydes and their low temperature (Z)->(E) isomerization induced by sulfur dioxide

Sulfur dioxide-mediated syntheses of polyfunctional alkenes and (E,Z)- and (E,E)-2,4-dien-1-ones

Long-distance effect on one-bond C-C scalar couplings upon introduction of a double bond in bicyclic systems

2,3,5,6-Tetrakis(Methylene)-1,4-Cyclohexanediyl (1,2,4,5-Tetramethylenebenzene), a Disjoint Non-Kekule Singlet Hydrocarbon Biradical

Functionalized pyrrolidines as alpha-mannosidase inhibitors and growth inhibitors of human glioblastoma and melanoma cells

Umpolung with Sulfur Dioxide: Carbon-Carbon Cross-Coupling of Electron-Rich 1,3-Dienes and Alkenes; Application to the Enantioselective Synthesis of Long-Chain Polyketide Fragments

Rational Design of 4-Aryl-1,2,3-Triazoles for Indoleamine 2,3-Dioxygenase 1 Inhibition

The spirocyclopropyl moiety as a methyl surrogate in the structure of L-fucosidase and L-rhamnosidase inhibitors

Synthesis of Rare Carbohydrates and Biomolecules from Furan

Silyl methallylsulfinates: efficient and powerful agents for the chemoselective silylation of alcohols, polyols, phenols and carboxylic acids