P-chiral phospholanes and phosphocyclic compounds and their...

Details P-chiral phospholanes and phosphocyclic compounds and their... P-chiral phospholanes and phosphocyclic compounds and their...

2006-09-12

2006-09-12

Richter, Johann (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Phosphorus containing

C568S012000, C568S070000, C568S073000, C564S114000

Reexamination Certificate

active

07105702

ABSTRACT:
Chiral ligands and metal complexes based on such chiral ligands useful in asymmetric catalysis are disclosed. The metal complexes according to the present invention are useful as catalysts in asymmetric reactions, such as, hydrogenation, hydride transfer, allylic alkylation, hydrosilylation, hydroboration, hydrovinylation, hydroformylation, olefin metathesis, hydrocarboxylation, isomerization, cyclopropanation, Diels-Alder reaction, Heck reaction, isomerization, Aldol reaction, Michael addition; epoxidation, kinetic resolution and [m+n] cycloaddition. Processes for the preparation of the ligands are also described.

REFERENCES:
patent: 5149878 (1992-09-01), Robertson et al.
patent: 5322956 (1994-06-01), Burk
patent: 5936109 (1999-08-01), Berens
patent: 6043396 (2000-03-01), Sturmer et al.
patent: 6492544 (2002-12-01), Krimmer et al.
patent: 6545183 (2003-04-01), Berens
patent: 6605745 (2003-08-01), Hoge et al.
patent: 2002/0087017 (2002-07-01), Hoge, II et al.
patent: 2004/0229846 (2004-11-01), Zhang et al.
CA:138:55724 abs of Organic Letters by Tang et al 4(23) pp. 4159-4161 2002.
CA:17:311163 abs of Angewandte Chemie International Edition by Tang et al 41(9) pp. 1612-1614 2002.
CA:103:215527 abs of Inorganic Chemistry by Mercier et al 24(24) pp. 4141-4149 1985.
He et al., Optical Resolution, Configurational Stability, and Coordination Chemistry of the P-Chiral Heterocyclic Diphosphine 1,1′-Diphenyl-3,3′,4,4′-tetramethyl-2′2-diphosphole-3′3′-diene, Organometallics, (1999), 18 (20), 4027-4031.
Bienewald et al., A New Ligand Containing a Unique Combination of Backbone and P-Centered Chirality: Synthesis, Resolution and Asymmetric Catalysis Using a Chiral Enatiopure 2, 2′-Biphospholene, Tetrahedron: Asymmetry, 10 (1999), 4701-4707.
Zublocka et al., Inverse Hydrozirconation: A Regio- and Diasterospecific Path to New Diphosphines, Angewandte Chemie, 1993, 105 (12), 1846-8.
Database CAPLUS on STN, Chemical abstracts CA:120:245287, Zublocka et al.—“Inverse hydrozirconation: a regio- and diastereospecific path to new diphosphines”, Angew Chem. Int. Ed. 1993, 32(12) pp. 1735-1737.
Database CAPLUS on STN, Chemical abstracts CA:123:228297, Zablocka et al. —“Unprecedented inversion of configuration at carbon in the electrophilic cleavage or the carbon-zirbondium(IV)bond”, Journ. Of the American Chem. Soc., 1995, 117(31) pp. 8083-8089.
Database CAPLLUS on STN, Chemical abstracts CA:123:144020, Bianchini et al. —“N new P-chiral aminophosphine ligand containing a 2, 2′-coupled pyrrolidine-phospholane ring system. Synethsis and coordination properties with rhodium(I)and iridium(I)fragments”, Journ. Of the American Chem. Soc., Chemical Communications, 1995, (8) pp. 833-834.
Database CAPLUS on STN, Chemical abstracts CA:119:72317, Von Matt et al.—“Chiral(phoshinoaryl)dihydrooxazoles as ligands in asymmetric catalysis: palladium-catalyzed allylic substitution”, Angewandte Chemie Int. Ed Engl. 1993, 32(4) pp. 566-568.
Database CAPLUS on STN, Chemical abstracts CA:124:76831, Field et al.—“Synthesis of New Bidentate Phosphine Ligands Containing Saturated Phosphorus Heterocycles”, Inorganic Chemistry, 1996, 35(9) pp. 2546-2548.
Ojima, “Catalytic asymmetric synthesis,” VCH, New York, 1993.
Noyori, “Asymmetric catalysis in organic synthesis,” John Wiley & Sons, Inc., New York, 1994.
Knowles, “Asymmetric Hydrogenation,” Ass. Chem. Res., 16, 106-112, 1983.
Krapcho et al., “2-Carbethoxycyclooctanone,” J. Org. Synth., 5, 198-201, 1973.
Yamago et al. “Tertiary phosphines and P-chiral phosphinites bearing a fullerene substituent,” J. Chem. Soc., Chem. Comm., 2093-2094, 1994.
Togni, “Planar-chiral ferrocenes: synthetic methods and applications.” Angew. Chem. Int. Ed. Engl., 35 No. 13/14, 1475-1477, 1996.
McKinstry et al. “An efficient procedure for the synthesis of elecron rich bisphosphines containing homochiral Backbones.” Tetrahedron Letters, vol. 35, No. 50, 9319-9322, 1994.
Zhu et al. “Highly efficient asymmetric synthesis of β-amino acid derivatives via rhodium-catalyzed hydrogenation of β-(acylamino)acrylates,” J. Org. Chem., 64, 6907-6910, 1999.
Gridnev et al. “Asymmetricd hydrogenation catalyzed by (S, S)-R-BisP-Rh and (R, R)-R-MiniPHOS Complexes: Scope, Limitations, and Mechanism,” Adv. Synth. Catal., 343, No. 1, 118-136, 2001.
Ohashi et al., “Highly enantioselective hydrogenation of a-dehydroamino acids by rhodium complexes with new unstmmetric p-chirogenic bisphosphine ligands,” Org. Lett., vol. 3, No. 3, 373-375, 2001.
Yamanoi et al. “Methylene-bridged p-chiral diphosphines in highly enantioselective reactions.” J. Org. Chem., 64, 2988-2989, 1999.
Blankenstein et al. “A new class of modular phosphinite-oxazoline ligands: Ir-catalyzed enantioselective hydrogenation of alkenes.” Angew. Chem. Int. Ed., 40, No. 23, 4445-4447, 2001.
Lightfoot et al. “Enantioselective hydrogenation of olefins with Iridium-Phosphanodihyrooxazole catalysts.” Angew. Chem. Int. Ed., 37, No. 20, 2897-2899, 1998.
Hou et al. “New, optically active phosphine oxazoline (JM-Phos) ligands: Syntheses and applications in allylation Reactions.” J. Org. Chem., 66, 206-215, 2001.
Zhou et al. Highly effective chiral ortho-substituted BINAPO ligands (o-BINAPO): applications in Ru-catalyzed asymmetric hydrogenations of β-aryl-substituted β-(acylamino)acrylates and β-keto esters, J. Am. Chem. Soc. 124, 4952-53, 2002.
Littke et al. “A versatile catalyst for heck reactions of aryl chlorides and aryl bromides under mild conditions.” J. Am. Chem. Soc., 123, 6989-7000, 2001.
Powell et al. “Chiral imidazolylidine ligands for asymmetric hydrogenation of aryl alkenes.” J. Am. Chem. Soc., 123 8878-8879, 2001.
Gridney et al. “Asymmetric hydrogenation of enamides with Rh-BisP and Rh-miniPHOS catalysts. Scope, Limitations, and Mechanism.” J. Am. Chem. Soc., 123, 5268-5276, 2001.
Zon et al. “The stereospecific desulfurization of acyclic phosphine sulfides with hexachlorodisilane and the alkaline Hydrolysis of monoalkoxy- and monoalkylmercaptophosphonium salts.” J. Am. Chem. Soc., 91:25, 7023-7027, 1969.
Imamoto et al. Synthesis and reactions of phosphine-boranes. Synthesis of new bidentate ligands Homochiral phosphine centers via optically pure phosphine-boranes, J. Am. Chem. Soc., 112, 5244-5252, 1990.
Maryanoff et al. A one-step synthesis of optically pure 1, 2-ethano bis sulfoxides and phosphine oxidesvia the Copper-promoted oxidative dimerization of chiral sulfinyl and phosphinyl carbanions, J. Am. Chem. Soc., 95:17, 5839-40, 1973.
Muci et al. “Enantioselective deprotonation as a vehicle for the asymmetric synthesis of C2-symmetric p-chiral Diphosphines.” J. Am. Chem. Soc., 117, 9075-9076, 1995.
Corey et al. “A new and highly enantioselective synthetic route to p-chiral phosphines and diphosphines.” J. Am. Chem. Soc., 115, 11000-11001, 1993.
Vineyard et al. “Asymmetric hydrogenation. Rhodium chiral bisphosphine catalyst.” J. Am. Chem. Soc., 99:18, 3946-3952, 1977.
Noyori et al. “BINAP: An efficient chiral element for asymmetric catalysis.” Acc. Chem. Res., 23, No. 10, 345-250, 1990.

Affiliated with

Also associated with

Rating

P-chiral phospholanes and phosphocyclic compounds and their... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with P-chiral phospholanes and phosphocyclic compounds and their..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and P-chiral phospholanes and phosphocyclic compounds and their... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3526591