(R)-H8-BINAP

Reaction

1. Biaryl bisphosphine ligand. The H8-BINAP ligand, as the ruthenium complex, catalyzes hydrogenation of unsaturated carboxylic acids to a higher ee than does BINAP.
2. The ruthenium catalyzed hydrogenation of aryl propenoic acid to produce the drug Ibuprofen.
3. Rhodium catalyzed asymmetric regioselective 1,4-addition of arylboronic acids to 3-substituted maleimides.
4. Ligand for palladium-catalyzed enantioselective hydrogenation of substituted indoles.
5. Rhodium-catalyzed enantioselective cyclization of γ-alkynylaldehydes with acyl phosphonates.
6. Enantioselective synthesis of axially chiral 1-arylisoquinolines by Rh-catalyzed [2+2+2] cycloaddition.
7. Enantioselective synthesis of 2,3-disubstituted indolines through Bronsted acid/Pd-complex-promoted tandem reactions.
8. Dehydration triggered asymmetric hydrogenation of 3-(α-hydroxyalkyl)indoles
9. Iridium-catalyzed [2+2+2] cycloaddition of α,ω-diynes with arylisocyanates
10. Asymmetric hydrogenation of 3-(toluenesulfonamidoalkyl)-indoles
11. Asymmetric Rh(I)-catalyzed intramolecular [3+2] cycloaddition of 1-yne-vinylcyclopropanes for bicyclo[3.3.0] compounds with a chiral quaternary carbon stereocenter.
12. Enantioselective intermolecular [2+2+2] cycloadditions of ene-allenes with allenoates.
13. Rh-catalyzed one-pot intermolecular [2+2+2] trimerization/asymmetric intramolecular [4+2] cycloaddition of two aryl ethynyl ethers and 5-alkynals.
14. Rh-catalyzed regio-, diastereo-, and enantioselective [2+2+2] cycloaddition of 1,6-enynes with acrylamides.

Uses

Catalytic ligand used for:

• Enantioselective synthesis of dihydrobenzofurans and dihydronaphthofurans via olefin isomerization/enantioselective intramolecular Alder-ene reaction of enynes catalyzed by Rh
• Preparation of axially chiral biaryl compounds by gold-catalyzed stereoselective intramolecular hydroarylation
• Preparation of chiral 3-alkyl-substituted indolines by tandem condensation-asymmetric hydrogenation of indoles with aldehydes, catalyzed by Bronsted acids and palladium BINAP complexes
• Stereoselective preparation of hydrindanes and decalins containing up to four contiguous stereocenters via rhodium-catalyzed [2+2+2] cycloaddition of ene-allenes with allenes
• Rhodium-catalyzed asymmetric formal olefination or cycloaddition of 1,3-dicarbonyl compounds with 1,6-diynes or 1,6-enynes
• Stereoselective preparation of 2,3-substituted indolines via Pd-catalyzed hydrogenation of (α-hydroxyalkyl)indoles

General Description

The product is a diphenylphosphinobenzoic acid (DPPBA) based ligand for the palladium-catalyzed asymmetric allylic alkylation with a high degree of enantioselectivity.