Browse
Submit Data
Databases
API
Help

Dataset Information

23 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Vinylsilanes in Highly Diastereo- and Regio-Selective Synthesis of Dihydropyrans.

ABSTRACT: Borontrifluoride etherate (BF₃·OEt₂) can be efficiently used for the synthesis of dihydropyrans from triethylsilyl homoallylic alcohols and aldehydes in good yields. The reaction is highly diastereo- and regio-selective.

SUBMITTER: Borthakur U

PROVIDER: S-EPMC6648048 | biostudies-literature | 2019 Feb

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Vinylsilanes in Highly Diastereo- and Regio-Selective Synthesis of Dihydropyrans.

Borthakur Upasana U Biswas Subhamoy S Saikia Anil K AK

ACS omega 20190204 2

Borontrifluoride etherate (BF<sub>3</sub>·OEt<sub>2</sub>) can be efficiently used for the synthesis of dihydropyrans from triethylsilyl homoallylic alcohols and aldehydes in good yields. The reaction is highly diastereo- and regio-selective. ...[more]

PMID: 31459498

Similar Datasets

Studies on the regio- and diastereo-selective epoxidation of daphnanes and tiglianes.

Project description:Daphnanes and tiglianes are diterpenes with a shared tricyclic 5-7-6 ring system. Many members exhibit significant biological activities often associated with protein kinase C signaling. Many of these natural products (~100) have a C6-C7 ?-epoxide whose influence on biological activity is little studied. Using the more readily available phorbol ester PDBu as a test substrate, we report an efficient, and potentially general, ?-epoxidation method based on a vanadium-catalyzed asymmetric epoxidation with bishydroxamic acid (BHA) ligands.

| S-EPMC4449265 | biostudies-literature

Chiral phosphine-catalyzed tunable cycloaddition reactions of allenoates with benzofuranone-derived olefins for a highly regio-, diastereo- and enantioselective synthesis of spiro-benzofuranones.

Project description:The first regioselective catalytic asymmetric [3 + 2] cycloaddition of benzofuranone-derived olefins with allenoates and substituted allenoates has been developed in the presence of (R)-SITCP, affording different functionalized 3-spirocyclopentene benzofuran-2-ones in good yields with high enantioselectivities under mild conditions. The substrate scope has also been examined. The regioselective outcomes for this phosphine-catalyzed [3 + 2] cycloaddition reaction can be rationalized using DFT calculations.

| S-EPMC5950759 | biostudies-literature

The regio- and stereochemical course of reductive cross-coupling reactions between 1,3-disubstituted allenes and vinylsilanes: Synthesis of (Z)-dienes.

Project description:In investigations aimed at exploring the potential of disubstituted allenes in stereoselective synthesis, we report studies that explore the reductive cross-coupling reaction of vinylsilanes with a range of substituted allenes. Regiochemical control is attained by employing allenic alkoxides, where the proximal heteroatom dictates the site-selectivity in a process that proceeds by net formal metallo-[3,3] rearrangement (directed carbometalation/elimination). Stereoselectivity in these reactions is complex, with both the nature of allene substitution and relative stereochemistry of the substrate impacting the stereoselective generation of each alkene of a substituted 1,3-diene. 2009 Elsevier Ltd. All rights reserved.

| S-EPMC3769195 | biostudies-literature

Highly diastereo- and enantioselective CuH-catalyzed synthesis of 2,3-disubstituted indolines.

Project description:A diastereo- and enantioselective CuH-catalyzed method for the preparation of highly functionalized indolines is reported. The mild reaction conditions and high degree of functional group compatibility as demonstrated with substrates bearing heterocycles, olefins, and substituted aromatic groups, renders this technique highly valuable for the synthesis of a variety of cis-2,3-disubstituted indolines in high yield and enantioeselectivity.

| S-EPMC4440622 | biostudies-literature

Hydroxy group-enabled highly regio- and stereo-selective hydrocarboxylation of alkynes.

Project description:Here we present an example of utilizing hydroxy groups for regioselectivity control in the addition reaction of alkynes-a highly efficient Pd-catalyzed syn-hydrocarboxylation of readily available 2-alkynylic alcohols with CO in the presence of alcohols with an unprecedented regioselectivity affording 3-hydroxy-2(E)-alkenoates. The role of the hydroxy group has been carefully studied. The synthetic potential of the products has also been demonstrated.

| S-EPMC6544123 | biostudies-literature

Mo-catalyzed regio-, diastereo-, and enantioselective allylic alkylation of 3-aryloxindoles.

Project description:A highly regio-, diastereo-, and enantioselective allylic alkylation reaction mediated by a chiral molybdenum catalyst has been developed as a novel entry into synthetically versatile 3-alkyl-3-aryloxindoles. Extremely bulky nucleophiles were employed to form a quaternary center and an adjacent tertiary center asymmetrically concurrently. The regio- and diastereoselectivity of the reaction is dependent upon the steric and electronic nature of the nucleophiles to an unusual degree. A reaction mechanism based on the bonding modes of molybdenum enolate complexes was discussed.

| S-EPMC2536500 | biostudies-literature

Ring-Opening Regio-, Diastereo-, and Enantioselective 1,3-Chlorochalcogenation of Cyclopropyl Carbaldehydes.

Project description:meso-Cyclopropyl carbaldehydes are treated in the presence of an organocatalyst with sulfenyl and selenyl chlorides to afford 1,3-chlorochalcogenated products. The transformation is achieved by a merged iminium-enamine activation. The enantioselective desymmetrization reaction, leading to three adjacent stereocenters, furnished the target products in complete regioselectivity and moderate to high diastereo- and enantioselectivities (d.r. up to 15:1 and e.r. up to 93:7).

| S-EPMC6680189 | biostudies-literature

Palladium-catalyzed regio-, diastereo-, and enantioselective benzylic allylation of 2-substituted pyridines.

Project description:We report a new method for the highly regio-, diastereo-, and enantioselective palladium-catalyzed allylic alkylation of 2-substituted pyridines that allows for the formation of homoallylic stereocenters containing alkyl, aryl, heteroaryl, and nitrogen substituents. When the reaction is conducted with asymmetric acyclic electrophiles, both linear and branched products may be obtained exclusively by selecting the appropriate regioisomeric starting material and ligand, an example of the "memory effect." Deuterium-labeling studies reveal that though no such phenomenon occurs with racemic cyclic electrophiles, the chiral ligand employed reacts kinetically faster with the enantiomer of the substrate for which it is "matched" and yet eventually converts all "mismatched" substrate to product.

| S-EPMC3235048 | biostudies-literature

Regio- and Diastereoselective Synthesis of Highly Substituted, Oxygenated Piperidines from Tetrahydropyridines.

Project description:Diastereoselective epoxidation and regioselective ring-opening methods were developed for the synthesis of densely substituted, oxygenated piperidines from two classes of tetrahydropyridines with distinct stereochemical displays of functionalities. A new and practical in situ prepared epoxidation reagent was developed for the diastereoselective epoxidation of one class of sterically hindered tetrahydropyridines. The novel bifunctional epoxidation reagent, 2-carboperoxy-3,4,5,6-tetrafluorobenzoic acid, was designed to incorporate highly reactive percarboxy acid and pendant carboxylic acid groups, which through hydrogen bonding to the amino group successfully overrode steric effects and directed epoxidation to occur at the more hindered face of the tetrahydropyridine. Nucleophilic ring-opening of the epoxides with water, alcohols, and HF proceeded with high regioselectivity, affording piperidinol products with adjacent tetrasubstituted carbons.

| S-EPMC4496584 | biostudies-literature

Highly Regio- and Stereoselective Catalytic Synthesis of Conjugated Dienes and Polyenes.

Project description:Conjugated dienes and polyenes are typically synthesized by sequential introduction of C?C bonds. Here, we report a practical and scalable, catalytic dienylation that is highly regio- and stereoselective for both C?C bonds. The reaction is enabled by a stereoselective palladium-catalyzed cross-coupling that is preceded by a regioselective base-induced ring opening of readily available sulfolenes. The dienylation reaction is particularly useful for the synthesis of synthetically challenging dienes containing cis double bonds. We also show that the reaction can serve as a synthetic platform for the construction of conjugated polyenes.

| S-EPMC6171353 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data