(S)-(+)-5,5'-Bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-4,4'-bi-1,3-benzodioxole,min.98%(S)-DTBM-SEGPHOS

Reaction

1. Biaryl bisphosphine ligand with narrow dihedral angle. The DTBM SEGPHOS® ligand, as the ruthenium complex, gives superior enantioselectivity and diastereoselectivity through dynamic kinetic resolution in the asymmetric hydrogenation of a-substituted-β-ketoesters useful in the synthesis of carbapenum antibiotics.
2. With rhodium, preferential enantioselective hydrogenation of more reactive olefin of extended enone structure.
3. Rhodium catalyzed chemo-, regio, and entantioselective [2 + 2 + 2] cycloaddition of alkynes with isocyanates.
4. With copper, enantioselective cross Aldol-type reaction of acetonitrile.
5. With copper, enantioselective vinylsilane alkenylation of aldehydes.
6. Gold carbene mediated stereoselective cyclopropanation of propargyl esters.
7. With copper, enantioselective 1,2-reduction of ketones, and 1,4-reduction of a α,β-usaturated esters.
8. With copper, catalytic enantioselective Mannich-type reaction.
9. Enantioselective fluorination of b β-keto esters, tert-butoxycarbonyl lactones and lactmes with Sodeoka's Pd-aqua complex and a fluorinating reagent.
10. Rh-catalyzed intramolecular olefin or carbonyl hydroacylation.

Uses

Catalytic ligand for:

• Enantioselective synthesis of secondary allylic alcohols via enantioselective reductions of α,β-unsaturated ketones
• Stereoselective preparation of cyclohexanone derivatives via rhodium-catalyzed rearrangement of allyl or allenic cyclobutanols
• Cu-catalyzed asymmetric conjugate reduction of beta-substituted unsaturated phosphonates to give optically active beta-stereogenic alkylphosphonates
• Asymmetric synthesis of cyclohexenones via Rh-catalyzed desymmetrization through enantioselective C-C bond activation and ring expansion of allenyl cyclobutanols
• Enantioselective synthesis and crystal structure of P-stereogenic alkynylphosphine oxides by Rh-catalyzed [2+2+2] cycloaddition