Unknown

Dataset Information

0

Asymmeric formal [3 + 3]-cycloaddition reactions of nitrones with electrophilic vinylcarbene intermediates.

ABSTRACT: With metal carbene access to dipolar intermediates, 3,6-dihydro-1,2-oxazines are produced in high yields by dirhodium(II) carboxylate catalyzed reactions between nitrones and a ?-TBSO-substituted vinyldiazoacetate. High enantiocontrol occurs with catalysis by N-phthaloyl-(S)-(amino acid)-ligated dirhodium carboxylates for [3 + 3]-cycloaddition reactions with both acyclic and cyclic nitrones.

SUBMITTER: Wang X 

PROVIDER: S-EPMC3192303 | biostudies-other | 2011 Oct

REPOSITORIES: biostudies-other

Json Xml
altmetric image

Publications

Asymmeric formal [3 + 3]-cycloaddition reactions of nitrones with electrophilic vinylcarbene intermediates.

Wang Xiaochen X   Xu Xinfang X   Zavalij Peter Y PY   Doyle Michael P MP  

Journal of the American Chemical Society 20110927 41

With metal carbene access to dipolar intermediates, 3,6-dihydro-1,2-oxazines are produced in high yields by dirhodium(II) carboxylate catalyzed reactions between nitrones and a β-TBSO-substituted vinyldiazoacetate. High enantiocontrol occurs with catalysis by N-phthaloyl-(S)-(amino acid)-ligated dirhodium carboxylates for [3 + 3]-cycloaddition reactions with both acyclic and cyclic nitrones. ...[more]

Similar Datasets

Unknown Ferrocenyl-substituted tetrahydrothiophenes via formal [3 + 2]-cycloaddition reactions of ferrocenyl thioketones with donor-acceptor cyclopropanes.
| S-EPMC7296194 | biostudies-literature
Unknown Non-precious metals catalyze formal [4 + 2] cycloaddition reactions of 1,2-diazines and siloxyalkynes under ambient conditions.
| S-EPMC4076001 | biostudies-literature
Unknown Synthesis of pyrrolo[1,2-<i>a</i>]quinolines by formal 1,3-dipolar cycloaddition reactions of quinolinium salts.
| S-EPMC6633155 | biostudies-literature
Unknown Formal [3+2] Cycloaddition Reactions of Electron-Rich Aryl Epoxides with Alkenes under Lewis Acid Catalysis Affording Tetrasubstituted Tetrahydrofurans.
| S-EPMC7036929 | biostudies-literature
Unknown Formal [4 + 2] cycloaddition of imines with alkoxyisocoumarins.
| S-EPMC6082175 | biostudies-literature
Unknown Cyano Diels-Alder and cyano ene reactions. Applications in a formal [2 + 2 + 2] cycloaddition strategy for the synthesis of pyridines.
| S-EPMC2944912 | biostudies-literature
Unknown Cycloaddition reactions for antiviral compounds
| S-EPMC7149647 | biostudies-literature
Unknown Formal [4 + 4]-, [4 + 3]-, and [4 + 2]-cycloaddition reactions of donor-acceptor cyclobutenes, cyclopropenes and siloxyalkynes induced by Bronsted acid catalysis.
| S-EPMC8179600 | biostudies-literature
Unknown Competition studies in alkyne electrophilic cyclization reactions.
| S-EPMC2662397 | biostudies-literature
Unknown Formal [2 + 2 + 2] cycloaddition strategy based on an intramolecular propargylic ene reaction/Diels-Alder cycloaddition cascade.
| S-EPMC2924204 | biostudies-literature