Unknown

Dataset Information

0

Synthesis of new pyrrolidine-based organocatalysts and study of their use in the asymmetric Michael addition of aldehydes to nitroolefins.

ABSTRACT: New pyrrolidine-based organocatalysts with a bulky substituent at C2 were synthesized from chiral imines derived from (R)-glyceraldehyde acetonide by diastereoselective allylation followed by a sequential hydrozirconation/iodination reaction. The new compounds were found to be effective organocatalysts for the Michael addition of aldehydes to nitroolefins and enantioselectivities up to 85% ee were achieved.

SUBMITTER: Castan A 

PROVIDER: S-EPMC5389197 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Synthesis of new pyrrolidine-based organocatalysts and study of their use in the asymmetric Michael addition of aldehydes to nitroolefins.

Castán Alejandro A   Badorrey Ramón R   Gálvez José A JA   Díaz-de-Villegas María D MD  

Beilstein journal of organic chemistry 20170327

New pyrrolidine-based organocatalysts with a bulky substituent at C2 were synthesized from chiral imines derived from (<i>R</i>)-glyceraldehyde acetonide by diastereoselective allylation followed by a sequential hydrozirconation/iodination reaction. The new compounds were found to be effective organocatalysts for the Michael addition of aldehydes to nitroolefins and enantioselectivities up to 85% ee were achieved. ...[more]

Similar Datasets

Unknown New hydrogen-bonding organocatalysts: Chiral cyclophosphazanes and phosphorus amides as catalysts for asymmetric Michael additions.
| S-EPMC3944119 | biostudies-literature
Unknown Asymmetric synthesis of functionalized cyclohexanes bearing five stereocenters via a one-pot organocatalytic Michael-Michael-1,2-addition sequence.
| S-EPMC4268544 | biostudies-literature
Unknown Asymmetric Organocatalytic Sulfa-Michael Addition to Enone Diesters.
| S-EPMC5856655 | biostudies-literature
Unknown H-bond donor-directed switching of diastereoselectivity in the Michael addition of α-azido ketones to nitroolefins.
| S-EPMC8152593 | biostudies-literature
Unknown Enantioselective Michael Addition of Cyclic ?-Diones to ?,?-Unsaturated Enones Catalyzed by Quinine-Based Organocatalysts.
| S-EPMC6152274 | biostudies-literature
Unknown Stereodivergent organocatalytic intramolecular Michael addition/lactonization for the asymmetric synthesis of substituted dihydrobenzofurans and tetrahydrofurans.
| S-EPMC4517160 | biostudies-literature
Unknown Efficacy of Selenourea Organocatalysts in Asymmetric Michael Reactions under Standard and Solvent-Free Conditions.
| S-EPMC8658871 | biostudies-literature
Unknown Development of the enantioselective addition of ethyl diazoacetate to aldehydes: asymmetric synthesis of 1,2-diols.
| S-EPMC3271135 | biostudies-literature
Unknown Enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinones to nitroalkenes catalyzed by binaphthyl-derived organocatalysts.
| S-EPMC3388856 | biostudies-literature
Unknown Catalytic asymmetric tandem Friedel-Crafts alkylation/Michael addition reaction for the synthesis of highly functionalized chromans.
| S-EPMC3701415 | biostudies-literature