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

Chemical Properties

Melting point	126-128°C
Boiling point	987.3±65.0 °C(Predicted)
storage temp.	under inert gas (nitrogen or Argon) at 2-8°C
form	Powder
color	off-white
InChIKey	ZNORAFJUESSLTM-UHFFFAOYSA-N
SMILES	COc1c(cc(cc1C(C)(C)C)P(c2cc(c(OC)c(c2)C(C)(C)C)C(C)(C)C)c3ccc4OCOc4c3-c5c6OCOc6ccc5P(c7cc(c(OC)c(c7)C(C)(C)C)C(C)(C)C)c8cc(c(OC)c(c8)C(C)(C)C)C(C)(C)C)C(C)(C)C
CAS DataBase Reference	210169-40-7

Reaction

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.
With rhodium, preferential enantioselective hydrogenation of more reactive olefin of extended enone structure.
Rhodium catalyzed chemo-, regio, and entantioselective [2 + 2 + 2] cycloaddition of alkynes with isocyanates.
With copper, enantioselective cross Aldol-type reaction of acetonitrile.
With copper, enantioselective vinylsilane alkenylation of aldehydes.
Gold carbene mediated stereoselective cyclopropanation of propargyl esters.
With copper, enantioselective 1,2-reduction of ketones, and 1,4-reduction of a α,β-usaturated esters.
With copper, catalytic enantioselective Mannich-type reaction.
Enantioselective fluorination of b β-keto esters, tert-butoxycarbonyl lactones and lactmes with Sodeoka's Pd-aqua complex and a fluorinating reagent.
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

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