, = 13.1, 7.2 Hz, 1H). 13 C{ 1 H} NMR (125.8 MHz, vol.2
1 (2s), 127.4 (d, J = 11.1 Hz), 128.0 (d, J = 10.2 Hz), 128.3, 128.4 (d, J = 9, 57.3 (dd, J = 10.9, 7.0 Hz), 83.6 (dd, J = 9, vol.5, pp.31-32 ,
HRMS (ESI/Q-TOF) calcd for C 40 H 43 B 2 NOP 2 Na, ? +71.1 (br.s), +110.6 (br.s), vol.2, pp.610-611, 0928. ,
, CHCl 3 ). 1 H NMR (500 MHz, CDCl 3 ): ? 0.42-1.46 (m, 6H), 1.28 (d, J = 6.6 Hz, 3H), 2.19 (d, J = 7.6 Hz, 3H), 4.02 (s, 5H), 4.09 (m, 1H), 4.33 (m, 1H), 4.40 (m, 2H), 4.58 (m, 1H), 5.14 (t, J = 9.4 Hz, 1H), 6.52-6.58 (m, 2H), 6.95-7.05 (m, 5H), 7.07-7.18 (m, 3H), 7.15-7.17 (m, 1H), 7.19-7.24 (m, 2H), 7.29-7.33 (m, 2H), 7.36-7.40 (m, 1H), 7.42-7.49 (m, 4H). 13 C{ 1 H} NMR (125.8 MHz, vol.3
3 Hz), 130.3 (d, J =2.4 Hz), 130.7 (d, J = 57, vol.128 ,
HRMS (ESI/Q-TOF) calcd for C 38 H 43 B 2 FeNOP 2 Na [M+Na] + : 692.2261; found: 692.2247. Anal. calcd for C 38 H 43 B 2 FeNOP 2 : C 68, CDCl 3 ): ? +71.7 (br.s), +106.9 (br.s). HRMS (ESI/Q-TOF) calcd for C 38 H 43 B 2 FeNOP, vol.21 ,
2-(?-Naphtylphenylphosphinito)-1-methyl-2-phenylethyl], Nmethylamino diphenylphosphine dichloropalladium complex 32. X-ray quality crystals were grown by slow evaporation of CH 2, 134.6 (d, J = 12.9 Hz), 134.8, 136.1 (d, J = 2.6 Hz). 31 P{ 1 H} NMR (121.5 MHz, vol.791, 1012. ,
, Slighty yellow crystals. 1 H NMR (500 MHz
, CDCl 3 ): ? 14.0 (d, J = 2.8 Hz), Hz, 3H), 4.83-4.95 (m, 2H), 7.20-7.33 (m, 7H), 7.36-7.53 (m, 10H), 7.55-7.59 (m, 1H), 7.72-7.83 (m, 4H), 7.85-7.90 (m, 1H), 8.06-8.17 (m, 4H). 13 C{ 1 H} NMR (125.8 MHz, vol.33
, J =, vol.56, issue.1
3 (d, J = 2.2 Hz), 131.6 (d, J = 2.5 Hz), 132.1 (d, J = 51.2 Hz), 132.6 (d, J =, vol.131, issue.1 ,
, 132.7 (d, J = 2.0 Hz), vol.132
8 Hz), 135.4 (d, J = 12.8 Hz), 135.4 (d, J = 12.8 to a one pot procedure. First, the AMPP*(BH 3 and the complex was used without further purification. 4.10.3. Dimethyl (1,3-diphenylallyl)malonate 28: 1 H NMR (300 MHz, vol.133 ,
, 2. The enantiomeric excess was determined by HPLC analysis on Chiralpack IA, 1.00 mL/min, Hz, 1H), 6.41 (d, J = 15.8 Hz, 1H), 7.09-7.28 (m, 10H). 13 C{ 1 H} NMR (75 MHz, vol.9
, Hz, 1H), 6.38 (dd, J = 15.8, 7.5 Hz, 1H), 6.61 (d, J = 15.8 Hz, 1H), 7.21-7.26 (m, 1H), 7.28-7.34 (m, 4H), 7.36-7.42 (m, 8H), 7.44-7.51 (m, 2H). 13 C{ 1 H} NMR
,
Phosphorus (III) Ligands in Homogeneous Catalysis: Design and Synthesis, 2008. ,
, , 2012.
Lewis base catalysis in organic synthesis ,
Chiral quaternary phosphonium salts: a new class of organocatalysts, Adv. Synth. Catal, vol.351, pp.9344-9411, 2009. ,
Asymmetric catalysis as a method for the synthesis of chiral organophosphorus compounds, Tetrahedron: Asymmetry, vol.25, pp.5771-5794, 2011. ,
P-chirogenic organocatalysts: application to the aza-Morita-Baylis-Hillman (aza-MBH) reaction of ketimines, J. Am. Chem. Soc, vol.49, pp.2765-2768, 2013. ,
Catalystenabled site-divergent stereoselective Michael reactions: overriding intrinsic reactivity of enynyl carbonyl acceptors, Angew. Chem. Int. Ed, vol.57, pp.5853-5860, 2018. ,
Enantioselective dearomative [3+2] cycloaddition of 2-nitrobenzofurans with aldehyde-derived Morita-Baylis-Hillman carbonates, Chem. Commun, vol.55, pp.9144-9147, 2019. ,
The aminophosphine-phosphinites and related ligands: synthesis, coordination chemistry and enantioselective catalysis, Coord. Chem. Rev, pp.178-180, 1998. ,
Recent advances in their design, coordination chemistry, and use in enantioselective catalysis, Agbossou, F. Chiral Aminophosphine-Phosphinites (AMPP) in Phosphorus Ligands in Asymmetric Catalysis: Synthesis and Applications, vol.242, pp.477-505, 2003. ,
Threophos: A new chiral aminophosphine phosphinite (AMPP) ligand highly efficient in asymmetric hydrovinylation of cyclohexa-1,3-diene catalyzed by Nickel complexes, J. Org, issue.7 ,
Aminophosphine phosphinites derived from chiral 1,2-diphenyl-2-aminoethanols: synthesis and application in rhodium-catalyzed asymmetric hydrogenation of dehydroamino acid derivatives, Tetrahedron: Asymmetry, vol.50, pp.1487-1494, 1977. ,
, J. Organometallics, vol.19, pp.5723-5732, 2000.
Versatile synthesis of chiral aminophosphine phosphinite (AMPPs) as ligands for enantioselective hydrogenation, Aminophosphine phosphinite (AMPP) and enantioselective hydrogenation of ketones: further developments, vol.6, pp.227-230, 1911. ,
Versatile synthesis of P-chiral (ephedrine) AMPP ligand via their borane complexes. Structural consequences in Rh-catalyzed hydrogenation of methyl ?-acetamidocinnamate, Tetrahedron: Asymmetry, vol.370, issue.9, pp.4729-4743, 1989. ,
,
Enantioselective hydrogenation catalysis aided by a ?-bonded calix[4]arene to a P-chirogenic aminophosphane phosphinite rhodium complex, Modular P-chirogenic aminophosphane-phosphinite ligands for Rh-catalyzed asymmetric hydrogenation: A new model for prediction of enantioselectivity, vol.29, pp.3622-3631, 2007. ,
Origin of stereoinduction by chiral aminophosphane phosphinite ligands in enantioselective catalysisi: asymmetric hydroformylation, Chem. Eur. J, vol.6, issue.11, pp.4293-4301, 2000. ,
C-bulky P-chirogenic organophosphorus compounds, Intern. Patent. EP, vol.18305304, 2018. ,
th ). (13) For a representative example of diastereoselective synthesis with dynamic resolution of binaphtylithium reagent, see: Clayden, 1926. ,
Sulfoxides as 'traceless' resolving agents for the synthesis of atropoisomers by dynamic or classical resolution, Tetrahedron, vol.60, pp.4387-4397, 2004. ,
Parallel synthesis and screening of polymer-supported phosphorusstereogenic aminophosphane-phosphite and -phosphinite ligands, Angew. Chem. Int. Ed, vol.47, pp.6602-6605, 2008. ,
,
Asymmetric transition-metal-catalyzed allylic alkylations: Applications in total synthesis, C.R. Chimie, vol.13, issue.16, pp.2921-2943, 2003. ,
Catalytic asymmetric allylic alkylation employing heteroatom nucleophiles: a powerful method for C-X bond formation, Chem. Sci, vol.1, pp.970-1010, 2010. ,
Palladium-catalyzed asymmetric allylic alkylation strategies for the synthesis of acyclic tetrasubstituted stereocenters, Process Res. Dev, vol.16, pp.1-30, 2012. ,
Palladium-catalyzed asymmetric allylic alkylation of cyclic dienol carbonates: efficient route to enantioenriched ?-butenolides bearing an all-carbon ?-quaternary stereogenic center ,
Kinetic resolution of 2-substituted 2,3-dihydro-4-pyridones by palladium-catalyzed asymmetric allylic alkylation: catalytic asymmetric total synthesis of Indolizidine (-)-209I, Angew. Chem. Int. Ed, vol.52, pp.5932-5935, 2013. ,
Palladium-catalyzed asymmetric allylic alkylation of 4-substituted isoxazolidin-5-ones: Straightforward access to ? 2,2 -amino acids ,
, Eur. J, vol.24, pp.4810-4814, 2018.
, Palladium-catalyzed asymmetric allylic alkylation of 3-substituted 1H-indoles and tryptophan derivatives with vinylcyclopropanes, J. Am. Chem. Soc, vol.140, pp.6710-6717, 2018.
Asymmetric synthesis of ?-quaternary ?-lactams through palladium-catalyzed asymmetric allylic alkylation, Org. Lett, vol.21, pp.603-607, 2019. ,
URL : https://hal.archives-ouvertes.fr/hal-02533178
,
Steric and electronic ligand perturbations in catalysis: asymmetric allylic substitution reactions using C 2 -symmetrical phosphorus-chiral (bi)ferrocenyl donors, J. Org. Chem, vol.66, pp.759-770, 2001. ,
A novel P-chirogenic phosphine ligand ,
Applications in asymmetric Pd-catalyzed allylic substitution and Ru-catalyzed hydrogenation, ethane: synthesis and use in rhodium-catalyzed asymmetric hydrogenation and palladium-catalyzed asymmetric allylic alkylation, vol.14, pp.7413-7416, 2001. ,
,
Clear evidence for both electronic effect and P-chirality driving enantioselectivity in Palladium-catalyzed allylations, Organometallics, vol.34, pp.4340-4358, 2015. ,
Kinetic resolution of 2,3-dihydro-2-substituted 4-quinolones by palladium-catalyzed asymmetric allylic alkylation, Angew. Chem. Int. Ed, vol.47, pp.1741-1744, 2008. ,
reaction/palladium catalyzed asymmetric allylic alkylation: access to chiral ?-enaminonitriles with excellent enantioselectivity, J. Org. Chem, vol.131, issue.23, pp.5080-5200, 2009. ,
A new optically pure half-sandwich Cp-Ru diphosphine complex with a chiral metal centre ,
Dynamic behaviour and X-ray analysis of chiral ? 3 -allylpalladium complexes, J. Organomet. Chem, vol.58, issue.25, pp.407-419, 1989. ,
A comparison of (R,R)-Me-DUPHOS and (R,R)DUPHOS-iPr ligands in the Pd 0 -catalysed asymmetric allylic alkylation reaction: Stereochemical and kinetic considerations, Eur. J. Org. Chem, vol.12, issue.27, pp.3498-3501, 1991. ,
Orally active benzamide antipsychotic agents with affinity for dopamine D 2 , serotonin 5-HT 1A , and adrenergic ? 1 receptors, J. Med. Chem, vol.41, 1997. ,
, Chem. Eur. J, vol.25, pp.1472-1475, 2019.
Ferrocenyl diphosphines containing stereogenic phosphorus atoms. Synthesis and application in the rhodium-catalyzed asymmetric hydrogenation, Eur. J. Org. Chem, vol.18, issue.29, pp.1041-1049, 1999. ,
Phosphorus-chiral analogues of 1,1'-bis(diphenylphosphino)ferrocene: asymmetric synthesis and application in highly enantioselective rhodium-catalyzed hydrogenation reactions, J. Org. Chem, vol.64, pp.3996-4004, 1999. ,
monodentate ferrocenyl phosphines, novel ligands for asymmetric catalysis, J. Org. Chem, vol.68, pp.156-166, 2003. ,
,
Xantphos Ligands and related ether diphosphines: Synthesis and application in rhodium-catalyzed asymmetric hydrogenation, ACS Catal, vol.7, pp.6162-6169, 2017. ,
Formation of diastereomerically pure oxazaphospholes and their reaction to chiral phosphane-borane adducts, Helv. Chim. Acta, vol.83, issue.33, pp.2930-2933, 2000. ,
Font-Bardia, M. P-Stereogenic monophosphines in Pd-catalyzed enantioselective hydrovinylation of styrene ,
P-Stereogenic phospholanes or phosphorinanes from o-biarylylphosphines: Two bridges not too far, Organomet. Chem, vol.696, pp.4665-4673, 2011. ,