Unknown

Dataset Information

0

Enantioselective ?-benzylation of aldehydes via photoredox organocatalysis.

ABSTRACT: The first enantioselective aldehyde ?-benzylation using electron-deficient aryl and heteroaryl substrates has been accomplished. The productive merger of a chiral imidazolidinone organocatalyst and a commercially available iridium photoredox catalyst in the presence of household fluorescent light directly affords the desired homobenzylic stereogenicity in good to excellent yield and enantioselectivity. The utility of this methodology has been demonstrated via rapid access to an enantioenriched drug target for angiogenesis suppression.

SUBMITTER: Shih HW 

PROVIDER: S-EPMC3056320 | biostudies-literature | 2010 Oct

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Enantioselective α-benzylation of aldehydes via photoredox organocatalysis.

Shih Hui-Wen HW   Vander Wal Mark N MN   Grange Rebecca L RL   MacMillan David W C DW  

Journal of the American Chemical Society 20101001 39

The first enantioselective aldehyde α-benzylation using electron-deficient aryl and heteroaryl substrates has been accomplished. The productive merger of a chiral imidazolidinone organocatalyst and a commercially available iridium photoredox catalyst in the presence of household fluorescent light directly affords the desired homobenzylic stereogenicity in good to excellent yield and enantioselectivity. The utility of this methodology has been demonstrated via rapid access to an enantioenriched d  ...[more]

Similar Datasets

Unknown Enantioselective alpha-trifluoromethylation of aldehydes via photoredox organocatalysis.
| S-EPMC3310169 | biostudies-literature
Unknown Enantioselective Formal ?-Methylation and ?-Benzylation of Aldehydes by Means of Photo-organocatalysis.
| S-EPMC5396335 | biostudies-other
Unknown Direct β-alkylation of aldehydes via photoredox organocatalysis.
| S-EPMC4333594 | biostudies-literature
Unknown Enantioselective α-Alkylation of Aldehydes by Photoredox Organocatalysis: Rapid Access to Pharmacophore Fragments from β-Cyanoaldehydes.
| S-EPMC4548807 | biostudies-literature
Unknown Enantioselective aerobic oxidative cross-dehydrogenative coupling of glycine derivatives with ketones and aldehydes <i>via</i> cooperative photoredox catalysis and organocatalysis.
| S-EPMC8159221 | biostudies-literature
Unknown Enantioselective ?-arylation of aldehydes via the productive merger of iodonium salts and organocatalysis.
| S-EPMC3082494 | biostudies-literature
Unknown Spin-Center Shift-Enabled Direct Enantioselective ?-Benzylation of Aldehydes with Alcohols.
| S-EPMC5896313 | biostudies-other
Unknown Enantioselective aldehyde alpha-nitroalkylation via oxidative organocatalysis.
| S-EPMC3259685 | biostudies-literature
Unknown Enantioselective direct ?-amination of aldehydes via a photoredox mechanism: a strategy for asymmetric amine fragment coupling.
| S-EPMC3786402 | biostudies-literature
Unknown The productive merger of iodonium salts and organocatalysis: a non-photolytic approach to the enantioselective alpha-trifluoromethylation of aldehydes.
| S-EPMC2880471 | biostudies-literature