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BINAP

Asymmetric hydrogenation has been achieved with dissolved Wilkinson type catalysts (A. J. Birch, 1976 D. Valentine, Jr., 1978 H.B. Kagan, 1978). The (R)- and (S)-[l,l -binaph-thalene]-2,2 -diylblsCdiphenylphosphine] (= binap ) complexes of ruthenium (A. Miyashita, 1980) and rhodium (A. Miyashita, 1984 R. Noyori, 1987) have been prepared as pure atrop-isomers and used for the stereoselective Noyori hydrogenation of a-(acylamino) acrylic acids and, more significantly, -keto carboxylic esters. In the latter reaction enantiomeric excesses of more than 99% are often achieved (see also M. Nakatsuka, 1990, p. 5586). [Pg.102]

The reaction of a halide with 2-butene-1,4-diol (104) affords the aldehyde 105, which is converted into the 4-substituted 2-hydroxytetrahydrofuran 106, and oxidized to the 3-aryl-7-butyrolactone 107[94], Asymmetric arylation of the cyclic acetal 108 with phenyl triflate[95] using Pd-BINAP afforded 109, which was converted into the 3-phenyllactone 110 in 72% ee[96]. Addition of a molecular sieve (MS3A) shows a favorable effect on this arylation. The reaction of the 3-siloxycyclopentene 111 with an alkenyl iodide affords the. silyl... [Pg.143]

Asymmetric cyclization using chiral ligands has been studied. After early attempts[142-144], satisfactory optical yields have been obtained. The hexahy-dropyrrolo[2,3-6]indole 176 has been constructed by the intramolecular Heck reaction and hydroaryiation[145]. The asymmetric cyclization of the enamide 174 using (S j-BINAP affords predominantly (98 2) the ( )-enoxysilane stereoisomer of the oxindole product, hydrolysis of which provides the ( l-oxindole aldehyde 175 in 84% yield and 95% ec. and total synthesis of (-)-physostig-mine (176) has been achieved[146]. [Pg.154]

Catalytic Asymmetric Hydroboration. The hydroboration of olefins with catecholborane (an achiral hydroborating agent) is cataly2ed by cationic rhodium complexes with enantiomericaHy pure phosphines, eg, [Rh(cod)2]BE4BINAP, where cod is 1,5-cyclooctadiene and BINAP is... [Pg.323]

Catalytic asymmetric hydrogenation was one of the first enantioselective synthetic methods used industrially (82). 2,2 -Bis(diarylphosphino)-l,l -binaphthyl (BINAP) is a chiral ligand which possesses a Cg plane of symmetry (Fig. 9). Steric interactions prevent interconversion of the (R)- and (3)-BINAP. Coordination of BINAP with a transition metal such as mthenium or rhodium produces a chiral hydrogenation catalyst capable of inducing a high degree of enantiofacial selectivity (83). Naproxen (41) is produced in 97% ee by... [Pg.248]

Ru(OCOCH2)2[(3)-BINAP]-(106)-catalyzed reduction of precursor olefin (107). The asymmetric synthesis of analgesic tetrahydroisoquinolines makes use... [Pg.248]

N O Y O R I Chiral homogeneous hydrogenation Homogeneous chiral hydrogenation ol unsaluraled alcohols, or cartMxyNc acids, enamides, ketones in the presence ol BINAP Ru or Rh complex 8 as catalyst. [Pg.276]

Cationic BINAP-palladium and platinum complexes 30a,b can catalyze highly enantioselective cycloaddition reactions of arylglyoxals with acyclic and cyclic... [Pg.171]

For imines, a-imino esters with an N-p-methoxyphenyl substituent (21b) also reacted with Danishefsky s diene in the presence of 10 mol% of CUCIO4-T0I-BINAP to give the corresponding adduct in high yield with good enantiomeric excess (Scheme 5.10). Remarkably, reverse enantioselectivity was observed when the a-imino esters 21a and 21b were used. This notable selectivity was explained by as-... [Pg.204]

For the activation of a substrate such as 19a via coordination of the two carbonyl oxygen atoms to the metal, one should expect that a hard Lewis acid would be more suitable, since the carbonyl oxygens are hard Lewis bases. Nevertheless, Fu-rukawa et al. succeeded in applying the relative soft metal palladium as catalyst for the 1,3-dipolar cycloaddition reaction between 1 and 19a (Scheme 6.36) [79, 80]. They applied the dicationic Pd-BINAP 54 as the catalyst, and whereas this type of catalytic reactions is often carried out at rt or at 0°C, the reactions catalyzed by 54 required heating at 40 °C in order to proceed. In most cases mixtures of endo-21 and exo-21 were obtained, however, high enantioselectivity of up to 93% were obtained for reactions of some derivatives of 1. [Pg.237]

A transition structure model was proposed which accounts for the high selectiv-ities obtained for some of the substrates [80]. In the structure shown in Scheme 6.37 the two phosphorus atoms of the Tol-BINAP ligand and the two car-... [Pg.237]


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AgOTf/BINAP

Arylation, rhodium-BINAP-catalyzed

Asymmetric BINAP

Atropisomer BINAP

Atropisomerically chiral ligand, BINAP

BINAP , structure

BINAP Diels-Alder reaction

BINAP Heck reaction

BINAP Rh catalysts

BINAP Silver(I)-Catalyzed Asymmetric Reactions

BINAP addition reactions

BINAP allylation

BINAP allylic alcohols

BINAP asymmetric hydrogenation

BINAP axial chirality

BINAP binaphthyl

BINAP catalysis

BINAP catalysis addition

BINAP catalyst system

BINAP catalysts

BINAP catalysts rhodium

BINAP complexes

BINAP core-functionalized dendrimers

BINAP cyclic substrates

BINAP dendritic

BINAP derivatives

BINAP double hydrogenation

BINAP enantioselective Heck reaction

BINAP fluorous

BINAP hgand, catalytic enantioselective

BINAP hydrogen incorporation

BINAP hydrogen shift

BINAP hydrogenations

BINAP hydrosilylation

BINAP immobilized

BINAP in Heck reaction

BINAP ligand amination reactions

BINAP ligand asymmetric Heck reactions

BINAP ligand derivatives

BINAP ligand formation

BINAP ligand hydrazones

BINAP ligand imines

BINAP ligand primary alkylamines

BINAP ligand primary arylamines

BINAP ligand triflates

BINAP ligand, Noyori catalytic

BINAP ligands asymmetric protonation

BINAP ligands hydrogenation

BINAP ligands, Noyori catalytic asymmetric

BINAP ligands, Noyori catalytic asymmetric hydrogenation

BINAP mechanism

BINAP molecular structure

BINAP monoxide

BINAP olefin isomerization

BINAP polymer-bound

BINAP prostaglandin synthesis

BINAP reductive coupling with

BINAP resolution

BINAP silver salt complexes

BINAP synthesis

BINAP unsaturated alcohols

BINAP, asymmetric Heck reaction

BINAP, in asymmetric hydrogenations

BINAP-AgOTf catalyst

BINAP-DIPEN

BINAP-DPEN catalyst

BINAP-Rh complexes

BINAP-Ru chemistry

BINAP-Ru complexes

BINAP-RuCL complexes

BINAP-based rhodium complexes

BINAP-ligated palladium

BINAP.AgF

BINAP.AgOTf complex

BINAP/BINOL

BINAP/ruthenium combinations

BINAPs

BINAPs

Backbones Binap

Biaryls, chiral BINAP

Bidentate phosphorus ligands BINAP

Binap Ru catalyst

Binap asymmetric activation

Binap catalyst complex

Binaphthyls binap)

Carbo-BINAP

Cationic rhodium /BINAP complex catalyst

Chiral bidentate phosphorus ligands BINAP

Chiral ligands BINAP

Cycloisomerization BINAP

Diam-BINAP

Enantioselective hydrogenation BINAP complexes

Heterocyclic BINAP analogues

Hydrogenation BINAP-RuCl2-catalyzed

Hydrosilylation BINAP-copper

Iridium-BINAP

Iridium/BINAP complex

Lewis binap complexes

Ligand, BINAP

Metal BINAP complexes

Organocatalysts BINAP

P-tol-BINAP

PS supported BINAP

Palladium BINAP catalysts

Palladium BINAP)

Palladium complexes BINAP

Palladium- -BINAP catalytic system

Pd -BINAP

Pd-BINAP complex

Phosphine oxide of BINAP

Phosphines BINAP

R-BINAP

Rh-BINAP

Rhodium , chiral “binap” complexes

Rhodium , chiral “binap” complexes asymmetric hydrogenation with

Rhodium BINAP

Rhodium-catalyzed hydrogenation BINAP

Ru-BINAP

RuCl2 -binap

Ruthenium , chiral “binap” complexes

Ruthenium -BINAP complexes

Ruthenium BINAP

Ruthenium BINAP analogues

Ruthenium-BINAP catalyst

Ruthenium-BINAP hydrogenation

Ruthenium-catalyzed hydrogenation BINAP

Silver BINAP complex

Silver-BINAP catalyst

Synthesis of the BINAP Ligand

Tol-BINAP

Tol-BINAP complexes

Tol-BINAP-AgF

Tol-BINAP-CuF

Xyl-BINAP

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