Unknown

Dataset Information

0

Enantio- and Diastereoselective Synthesis of Homoallylic ?-Trifluoromethyl Amines by Catalytic Hydroalkylation of Dienes.

ABSTRACT: We describe a strategy for the enantio- and diastereoselective synthesis of homoallylic ?-trifluoromethyl amines by the catalytic hydroalkylation of terminal dienes. Trifluoromethyl-substituted isatin-derived azadienolate nucleophiles undergo ?-selective alkylation with a Pd-DTBM-SEGPHOS catalyst, which additionally promotes regioselective addition to the diene and delivers products in up to 86% yield, 10:1 dr, and 97.5:2.5 er.

SUBMITTER: Onyeagusi CI 

PROVIDER: S-EPMC7079280 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Enantio- and Diastereoselective Synthesis of Homoallylic α-Trifluoromethyl Amines by Catalytic Hydroalkylation of Dienes.

Onyeagusi Chibueze I CI   Shao Xinxin X   Malcolmson Steven J SJ  

Organic letters 20200204 4

We describe a strategy for the enantio- and diastereoselective synthesis of homoallylic α-trifluoromethyl amines by the catalytic hydroalkylation of terminal dienes. Trifluoromethyl-substituted isatin-derived azadienolate nucleophiles undergo γ-selective alkylation with a Pd-DTBM-SEGPHOS catalyst, which additionally promotes regioselective addition to the diene and delivers products in up to 86% yield, 10:1 dr, and 97.5:2.5 er. ...[more]

Similar Datasets

Unknown Diastereoselective synthesis of vicinal tertiary and <i>N</i>-substituted quaternary stereogenic centers by catalytic hydroalkylation of dienes.
| S-EPMC6013916 | biostudies-literature
Unknown Intermolecular Hydroamination of 1,3-Dienes To Generate Homoallylic Amines.
| S-EPMC6563820 | biostudies-literature
Unknown Direct catalytic enantio- and diastereoselective ketone aldol reactions of isocyanoacetates.
| S-EPMC4678506 | biostudies-literature
Unknown Enantio- and diastereoselective synthesis of (R,R)-beta-methoxytyrosine.
| S-EPMC2688733 | biostudies-literature
Unknown Diastereoselective construction of functionalized homoallylic alcohols by Ni-catalyzed diboron-promoted coupling of dienes and aldehydes.
| S-EPMC2676113 | biostudies-literature
Unknown Catalytic asymmetric reductive hydroalkylation of enamides and enecarbamates to chiral aliphatic amines.
| S-EPMC7910428 | biostudies-literature
Unknown Catalytic Enantio- and Diastereoselective Cyclopropanation of 2-Azadienes for the Synthesis of Aminocyclopropanes Bearing Quaternary Carbon Stereogenic Centers.
| S-EPMC6790987 | biostudies-literature
Unknown Palladium(II)-catalyzed enantio- and diastereoselective synthesis of pyrrolidine derivatives.
| S-EPMC3459323 | biostudies-literature
Unknown Enantio- and diastereoselective synthesis of N-acetyl dihydrotetrafibricin methyl ester.
| S-EPMC3679187 | biostudies-literature
Unknown An Enantio- and Diastereoselective Chemoenzymatic Synthesis of ?-Fluoro ?-Hydroxy Carboxylic Esters.
| S-EPMC5074308 | biostudies-literature