948047-90-3

Upstream product

• 14086-08-9 (R)-2-(2-furyl)-1,2-ethanediol 
• 98-59-9 p-toluenesulfonyl chloride 
• 2873-29-2 D-glucal triacetate 

Downstream Products

• 27948-61-4 (R)-(+)-1-(2-furyl)ethanol 
• 1007402-88-1 (R)-1-(furan-2-yl)-2-(tosyloxy)ethyl pivalate 
• 1007402-76-7 (R)-2-(tert-butyldimethylsilyloxy)-2-(furan-2-yl)ethyl 4-methylbenzenesulfonate 
• 1202865-70-0 C₂₉H₃₂O₅SSi 
• 1289257-56-2 C₂₂H₃₄O₅SSi 

Relevant academic research and scientific papers

Developing a diastereoselective intramolecular [4 + 3] cycloaddition of nitrogen-stabilized oxyallyl cations derived from N-sulfonyl-substituted allenamides

Efforts toward achieving a practical and diastereoselective intramolecular [4 + 3] cycloaddition of nitrogen-stabilized oxyallyl cations with tethered dienes are described. Epoxidation of N-sulfonyl substituted allenamides with dimethyldioxirane (DMDO) generates nitrogen-stabilized oxyallyl cations that readily undergo stereoselective [4 + 3] cycloaddition with dienes. Selectivity is found to depend on the tethering length as well as the stability of the oxyallyl cation intermediate, whether generated from N-carbamoyl- or N-sulfonyl-substituted allenamides. The use of chiral N-sulfonyl-substituted allenamides provided minimal diastereoselectivity in the cycloaddition, while high diastereoselectivity can be achieved with a stereocenter present on the tether. These studies provide further support for the synthetic utility of allenamides.

Stereoselective synthesis of 2,3,4-trisubstituted tetrahydrothiophenes

We describe an efficient new approach for the synthesis of highly substituted chiral tetrahydrothiophenes, based on the oxidation of a chiral furan substrate with singlet oxygen, followed by intramolecular hetero Michael addition.

Rapid access to in situ generated (R)- and (S)-2-furyloxirane and associated regioselective nucleophilic ring-opening studies

Reported herein is the facile preparation of (R)- and (S)-2-furyloxirane from D- and L-tri-O-acetyl glucal and associated regioselective nucleophilic ring-opening studies. Georg Thieme Verlag Stuttgart.

Approach to a better understanding and modeling of (S)-dihydrofuran-2-yl, (S)-tetrahydrofuran-2-yl-, and furan-2-yl-β-dialkylaminoethanol ligands for enantioselective alkylation

This paper outlines our efforts to study the influence of an oxygen atom adjacent to the stereogenic center of β-aminoalcohol derivatives used as ligands for catalysts in the asymmetric alkylation of aldehydes. Thirty-four enantiomerically pure (S)-dihydrofuran-2-yl, (S)-tetrahydrofuran-2-yl-, and furan-2-yl-β-dialkylamino alcohols have been prepared from 1,4:3,6-dianhydromannitol, 1,4:3,6-dianhydrosorbitol, and aminoacids, and then have been evaluated as ligands for the enantioselective addition of diethylzinc to benzaldehyde. Attention has been focused on the structural features governing the extent of chiral induction, the reaction rate, and the chemical yield of 1-phenyl-1-propanol which has been promoted by this wide collection of β-dialkylamino alcohols.

Chirality transfer from the furan ring transfer reaction

The furan ring transfer (FRT) reactions of optically active propynyl ethers [(1) and (2)] are described, facile chirality transfer from the cycloadduct to the allylic carbon of the product being observed; the stereochemistry of the product was determined