Product Name
(S)-(-)-5,5'-Bis(diphenylphosphino)-4,4'-bi-1,3-benzodioxole, min. 98% (S)-(-)-SEGPHOS
Certificate of Analysis (COA)
IUPAC Name
4-(5-diphenylphosphanyl-1,3-benzodioxol-4-yl)-1,3-benzodioxol-5-yl-diphenylphosphane
InChI Key
RZZDRSHFIVOQAF-UHFFFAOYSA-N
SMILES
C1OC2=C(O1)C(=C(C=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)C5=C(C=CC6=C5OCO6)P(C7=CC=CC=C7)C8=CC=CC=C8
Technical Notes:
1. Biaryl bisphos phine ligand with narrow dihedral angle. The SEGPHOS® ligand has been applied to a variety of metal catalyzed reactions. In many cases, yields and enantios electivities, exceed results obtained earlier using BINAP
2.As ruthenium complex, SEGPHC S® generally gives higher levels of chiral induction in as ymmetric hydrogenations of a,ß,and y-functionalized ketones. See ruthenium complexes 44-0096, 44-0518, 44-01 68
3.Used in Rh-catalyzed transformations such as: (a) 1,4-addition of boronic acids to coumarins, (b) addition of titanium reagents to imines,' (c) cotrimerization of alkenes and acetylenes,o (d) double 2+2+2 cycloaddition," (e) indanone formation.a,
4.Used in Pd-catalyzed transformations such as: (a) cycloaddition of 1,6-enyne, (b) arylative cyclization of allenyl aldehydes with boronic acids,13 (c) synthesis of chromans.
5.Used in Cu-catalyzed transformations such as: (a) nitroso Diels-Alder,' (b) reductive aldol
6.condensation, (c) conjugate reduction of unsaturated sulfones, and phophonates
7.Iridium-catalyzed asymmetric hydrogenation of quinolines activated by chloroformates
8.Iridium-catalyzed asymmetric transfer hydrog enation used in polyketide construction.
9.Rhodium-catalyzed asymmetric hydroarylation of 3-pyrrolines.
10.P alladium-catalyzed regio- and enantioselective dearomatization of pyrroles to 2H-pyrroles.' Rhodium-catalyzed as ymmetric synthesis of cyclopentanols.0
11. Silver-catalyzed as ymmetric Mannich-type reac tion.
Atroposelective catalysis
Publication Name: Nature reviews. Chemistry
Publication Date: 2024-06-18
DOI: 10.1038/s41570-024-00618-x