Unknown

Dataset Information

0

Asymmetric intramolecular arylcyanation of unactivated olefins via C-CN bond activation.

ABSTRACT: The enantioselective, intramolecular arylcyanation of unactivated olefins via C-CN bond activation has been accomplished using a Ni(0) catalyst and BPh3 co-catalyst. High enantioselectivities are achieved using TangPHOS as a chiral ligand. This method allows the generation of two new C-C bonds and one new quaternary carbon stereogenic center in a single synthetic step, converting readily available benzonitrile substrates into 1,1-disubstituted indanes in 49-85% yield and 92-97% ee.

SUBMITTER: Watson MP 

PROVIDER: S-EPMC2596758 | biostudies-literature | 2008 Sep

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Asymmetric intramolecular arylcyanation of unactivated olefins via C-CN bond activation.

Watson Mary P MP   Jacobsen Eric N EN  

Journal of the American Chemical Society 20080830 38

The enantioselective, intramolecular arylcyanation of unactivated olefins via C-CN bond activation has been accomplished using a Ni(0) catalyst and BPh3 co-catalyst. High enantioselectivities are achieved using TangPHOS as a chiral ligand. This method allows the generation of two new C-C bonds and one new quaternary carbon stereogenic center in a single synthetic step, converting readily available benzonitrile substrates into 1,1-disubstituted indanes in 49-85% yield and 92-97% ee. ...[more]

Similar Datasets

Unknown Strong and Confined Acids Catalyze Asymmetric Intramolecular Hydroarylations of Unactivated Olefins with Indoles.
| S-EPMC7830113 | biostudies-literature
Unknown Mechanistic Model for Enantioselective Intramolecular Alkene Cyanoamidation via Palladium-Catalyzed C-CN Bond Activation.
| S-EPMC5535300 | biostudies-literature
Unknown Catalytic diamination of olefins via N-N bond activation.
| S-EPMC4270412 | biostudies-other
Unknown Intramolecular aminocyanation of alkenes by N-CN bond cleavage.
| S-EPMC4077192 | biostudies-literature
Unknown Asymmetric synthesis of (-)-incarvillateine employing an intramolecular alkylation via Rh-catalyzed olefinic C-H bond activation.
| S-EPMC2713182 | biostudies-literature
Unknown Intramolecular Acetyl Transfer to Olefins by Catalytic C-C Bond Activation of Unstrained Ketones.
| S-EPMC5798000 | biostudies-literature
Unknown Pyrrolidine and piperidine formation via copper(II) carboxylate-promoted intramolecular carboamination of unactivated olefins: diastereoselectivity and mechanism.
| S-EPMC2590667 | biostudies-literature
Unknown Hydromethylation of Unactivated Olefins.
| S-EPMC4490774 | biostudies-literature
Unknown Enantioselective intramolecular hydroarylation of alkenes via directed C-H bond activation.
| S-EPMC2610454 | biostudies-literature
Unknown Catalytic asymmetric allylic and homoallylic diamination of terminal olefins via formal C-H activation.
| S-EPMC2776772 | biostudies-literature