Ewaluacja chiralnych atropoizomerycznych ligandów fosfinowych w procesach asymetrycznych katalizowanych kompleksami metali przejściowych Część 1: Ocena efektów sterycznych

• Autorzy: Demchuk O. , Łastawiecka E. , Pietrusiewicz K.M.

Warianty tytułu

EN

Evaluation of the efficiency of chiral atropisomeric phosphine ligands in asymmetric processes catalyzed by transition metal salts Part 1: Evaluation of steric effects

• Języki publikacji: PL

Abstrakty

PL

Asymetryczne reakcje są jednymi z najbardziej ekonomicznych, przyjaznych środowisku, oraz chętnie wykorzystywanymi w przemyśle farmaceutycznym transformacjami organicznymi. Niemniej jednak z powodu braku ogólnej teorii więżącej budowę katalizatorów z stereoselektywnością syntezy dobór odpowiedniego katalizatora dla nowej reakcji powinien odbywać się empirycznie. Ideą niniejszego przeglądu jest wyłonienie zależności pomiędzy budową katalizatora a jego efektywnością, co może znaleźć przełożenie na łatwiejszy dobór optymalnego układu katalitycznego.

EN

Asymmetric synthesis with the use of chiral complexes of transition metals is one of the most economic and environment friendly organic transformations applied in the pharmaceutical industry. However, due to the lack of a universal theory that would bind catalyst structure with synthesis stereoselectivity, selecting an appropriate catalyst for a new reaction is still performed empirically. The aim of this review is to indicate relations between catalyst structure and its efficiency, which may in the future facilitate the selection of an optimum catalytic system.

Słowa kluczowe

PL

chiralne fosfiny; ligandy atropoizomeryczne; ligandy fosforowe; kataliza asymetryczna

EN

chiral phosphines; atropisomeric ligands; phosphorus ligands; asymmetric catalysis

• Wydawca: Stowarzyszenie Inżynierów i Techników Przemysłu Chemicznego, ZW CHEMPRESS-SITPChem
• Czasopismo: Chemik
• Rocznik: 2012
• Tom: Vol. 66, nr 7
• Strony: 758--770

Twórcy

autor

Demchuk O.

autor

Łastawiecka E.

autor

Pietrusiewicz K.M.

Bibliografia

• 1. Noyori R.: Asymmetric Catalysis in Organic Synthesi. J.Wiley, NY, 1994.
• 2. Noyori R.: Asymmetric Catalysis: Science and Opportunities (Nobel Lecture 2001), Adv. Synth. Catal. 2003, 345, 15.
• 3. Noyori R., Takaya H.: BINAP: an efficient chiral element for asymmetric catalysis. Acc. Chem. Res. 1990, 23, 345.
• 4. Whitesell J. K.: C2 symmetry and asymmetric induction. Chem. Rev. 1989, 89, 1581.
• 5. Kienzle F., Lalonde M., Schmid R., Wang S.: Racemization of atropisomeric bis(phosphine oxide) compounds. Patent USA, 6,288,280, 2000.
• 6. Jacobsen E. N., Pfaltz A., Yamamoto Y.: Comprehensive Asymmetric Catalysis, Vol. 1-3, Springer-Verlag, Berlin, 1999, str. 1439
• 7. Ojima I.: Catalytic Asymmetric Synthesis.2 ed., J.Wiley-VCH, Weinheim, 2000.
• 8. Zastosowana w tym tekście numeracja ligandów rozpoczyna się dużą literą L, liczba odpowiada niezmienionemu rdzeniowi biarylowemu a mata litera odnosi się do modyfikacji funkcji fosforowej.
• 9. Noyori R.: Asymmetric Catalysis: Science and Opportunities (Nobel Lecture). Angew. Chem., Int. Ed. 2002, 41, 2008.
• 10. Knowles W. S.: Asymmetric Hydrogenations (Nobel Lecture). Angew. Chem., Int. Ed. 2002,41, 1998.
• 11. Sharpless K. B.: Searching for New Reactivity (Nobel Lecture). Angew. Chem., Int. Ed. 2001, 41, 2024.
• 12. Gennari C., Piarulli U.; Combinatorial Libraries of Chiral Ligands for Enantioselective. Catalysis, Chem. Rev. 2003, 103, 3071.
• 13. a) Murata M., Yamamoto N., Yoshikawa K., Morimoto T., Achiwa K.: Synthesis of atropisomeric biphenylbisphosphine, 6,6'-bis(dicyclohexylphosphino)-3,3'-dimethoxy-2,2',4,4'-tetramethyl-1, I '-biphenyl and its use in rhodium(I)-catalyzed asymmetric hydrogenation. Chem. Pharm. Bull. 1991, 39, 2767; b) Yoshikawa K., Yamamoto N., Murata M., Awano K., Morimoto T., Achiwa K.: A new type of atropisomeric biphenylbisphosphine ligand, (R)-MOC-BIMOP and its use in efficient asymmetric hydrogenation of a-aminoketone and ita-conic acid. Tetrahedron: Asymmetry 1992, 3, 13; c) Fujie N., Matsui M., Achiwa K.: Synthesis of New Atropisomeric Bisphosphine Ligands Bearing Chiral Phospholane and Their Use in Asymmetric Hydrogenation. Chem. Pharm Bull. 1999, 47, 436; d) Schmid R., Broger E. A., Cereghetti M., Crameri Y., Foricher J., Lalonde M., Muller R. K., Scalone M., Schoettel G., Zutter U.: New developments in enantioselective hydrogenation. Pure & Appl. Chem. 1996, 68, 131; e) Miyashita A., Karino H., Shimamura J., Chiba T., Nagano K., Nohira H., Takaya H.: Synthesis of Atropisomeric 2,2'-Bis(dicyclohexylphosphino)-6,6'-dimethyl-l,1 '-biphenyl (BICHEP) and Its Use in Rh(I)-catalyzed Asymmetric Hydrogenation of Prochiral Olefins. Chem. Lett. 1989, 1849; f) Jendralla H., Li C. H., Paulus E.: Efficient synthesis of (R)- and (S)-(6,6'-difluorobiphenyl-2,2'-diyl) bis(diphenylphosphine); Electron-poor biphenyl-type ligands for transition metal catalysts. Tetrahedron: Asymmetry 1994, 5, 1297; g) Hayashi T., SendaT., Takaya Y., Ogasawara M.: Rhodium-Catalyzed Asymmetric 1,4-Addition to l-Alkenylphosphonates. J. Am. Chem. Soc. 1999, 121, 11591; h) Wan K., Davis M. E.: Ruthenium (II)-sulfonated BINAP: A novel water-soluble asymmetric hydrogenation catalyst. Tetrahedron: Asymmetry 1993, 4, 2461; i) Zhang X., Mashima K., Koyano K., Sayo N., Kumobayashi H., Akutagawa S., Takaya H.: Synthesis of partially hydrogenated BINAP variants, Tetrahedon Lett. 1991, 32, 7283.
• 14. Bahrmann H., Bergrath K., Leiner H., Lappe P., Naumann C., Peters D., Regnat D.: BIN AS - synthesis and use of a new ligand for propylene hydroformylation. J. Organomet Chem. 1996, 520, 97.
• 15. Toriumi K., Ito T., Takaya H., Souchi T., Noyori R.: (8,9,10-trinorborna-2,5-diene)rhodium(I) perchlorate, the precursor of a catalyst for highly enantioselective hydrogenations. Acta Crystallogr., Sect.B: Struct. Crystallogr. Cryst. Chem. 1982, 38, 807.
• 16. Demchuk O.: nie publikowane. Obliczenia DFT (B3LYP, 6-31G* pseudoponetnial) zostały wykonane dla izolowanych cząsteczek w temp. pok. z wykorzystaniem programu Spartan'08.
• 17. Horiuchi T., Ohta T., Stephan M., Takaya H.: Structure and absolute configuration of [(+)589-(R)-2,2'-bis(diphenylphosphino)-1,1 '-binaphthyl]Synthesis of (R)- and (S)-7,7'-bis(diphenylphosphino)-2,2'-dimethoxy-l, l'-binaphthyl, a new axially dissymmetric bis(triarylphosphine). Tetrahedron: Asymmetry 1994,5,325.
• 18. Inagaki K., Nozaki K., Takaya H., Asymmetric Michael Reaction of α-Cyano Esters by Chiral Rh(I) Complex with a New Optically Active Bisphosphine Ligand, Synlett 1997, 119.
• 19. Lustenberger P, Diederich F.: Towards Asymmetric Catalysis in the Major Groove of I, I'-Binaphthalenes. Helv. Chim. Acta 2000, 83, 2865.
• 20. Trost B. M., Bunt R. C.: Asymmetric induction in allylic alkylations of 3-(acyloxy)cycloalkenes, J. Am. Chem. Soc. 1994, 116, 4089.
• 21. Schmid R., Cereghetti M., Heiser B., Schounholzer P, Hansen H. J.: Axially Dissymmetric Bis(triaryl)phosphines in the Biphenyl series: Synthesis of (6,6'-dimethylbiphenyl-2,2'-diyl)bis(diphenylphosphine) ('BIPHEMP') and analogues, and their use in Rh (I)-catalyzed asymmetric isomerizations of N.N-diethylnerylamine. Helv.Chim. Acta 1988, 71, 897.
• 22. Schmid R., Foricher J., Cereghetti M., Schounholzer P.: Axially Dissymmetric Diphosphines in the Biphenyl Series: Synthesis of (6,6'-Dimethoxybiphenyl-2,2'-diyl)bis(diphenylphosphine) ('MeO-BIPHEP') and Analogues via an ortho-Lithiation/lodination Ullmann-Reaction Approach. Helv. Chim. Acta 1991, 74, 370.
• 23. Zhang Z. G., Qian H., Longmire J., Zhang X. M.: Synthesis of Chiral Bi-sphosphines with Tunable Bite Angles and Their Applications in Asymmetric Hydrogenation of ß-Ketoesters, J. Org. Chem. 2000, 65, 6223.
• 24. Wu S., Wang W., Tang W., Lin M., Zhang X.: Highly Enantioselective Hydrogenation of Enol Acetates Catalyzed by Ru-TunaPhos Complexes. Org. Lett. 2002, 4,4495.
• 25. a) Lei A., Wu S He M., Zhang X.: Highly Enantioselective Asymmetric Hydrogenation of a-Phthalimide Ketone: An Efficient Entry to Enantiomerically Pure Amino Alcohols.]. Am. Chem. Soc. 2004, 126, 1626; b) Tang W., Wu S., Zhang X.: Enantioselective Hydrogenation of Tetrasubstituted Olefins of Cyclic ß-(Acylamino)acrylates. J. Am. Chem. Soc. 2003, 125, 9570.
• 26. Qiu L., Kwong F. Y., Wu J., Lam W. H., Chan S., Yu W.Y., Li Y.M., Guo R., Zhou Z., Chan A. S. C.: A new class of versatile chiral-bridged atropisomeric diphosphine ligands: remarkably efficient ligand syntheses and their applications in highly enantioselective hydrogenation reactions. J. Am. Chem. Soc. 2006, 128, 5955.
• 27. Wang C., Yang G., Zhuang J., Hang W.: From tropos to atropos: 5,5'-bridged 2,2'-bis(diphenylphosphino)biphenyls as chiral ligands for highly enantioselective palladium-catalyzed hydrogenation of α-phthalimide ketones. Tetrahedron Lett. 2010,51,2044.
• 28. Trabesinger G., Albinati A., Feiken N., Kunz R. W.: Pregosin P. S., Tschoerner M., Enantioselective Homogeneous Catalysis and the "3,5-Dialkyl Meta-Effect". MeO-BIPHEP Complexes Related to Heck, Allylic Alkylation, and Hydrogenation Chemistry. J. Am. Chem. Soc. 1997, 119, 6315.
• 29. Mashima K., Kusano K., Sato N., Matsumura Y., Nozaki K., Kumobayashi H., Sayo N., Hori Y., Ishizaki T., Akutagawa S., Takaya H.: Cationic BINAP-Ru(II) Halide Complexes: Highly Efficient Catalysts for Stereoselective Asymmetric Hydrogenation of α- and ß-Functionalized Ketones. J. Org. Chem. 1994, 59, 3064.
• 30. Morimoto T., Chiba M., Achiwa K.: Effects of the diarylphosphino groups of modified diops on the enantioselectivity and the catalytic activity of their rhodium (I) complexes in the catalytic asymmetric hydrogenations of enamides, Chem. Pharm. Bull. 1992, 40, 2894.
• 31. Knowles W.S.: Asymmetric hydrogenation. Acc. Chem. Res. 1983, 16, 106.
• 32. Pfaltz A.: Design of Chiral Ligands for Asymmetric Catalysis: From C2-Symmetric Semicorrins and Bisoxazolines to Non-Symmetric Phosphino-oxazolines. Acta Chem. Scand. 1996,50, 189.
• 33. Mashima K., Matsumura Y., Kusano K., Kumobayashi H., Sayo N., Hori Y., Ishizaki T., Akutagawa S., Takaya H.: Highly stereoselective asymmetric hydrogenation of 2-benzamidomethyl-3- oxobutanoate catalysed by cationic binap-ruthenium(II) complexes. J. Chem. Soc., Chem. Commun. 1991, 609.
• 34. Trabesinger G., Albinati A., Feiken N., Kunz R., Pregosin P S., Tschoerner M.: Enantioselective homogeneous catalysis and the '3,5-dialkyl meta- effect'. MeO-BIPHEP complexes related to heck, allylic alkylation, and hydrogenation chemistry. J.Am. Chem. Soc., 1997, I 19, 6315.
• 35. Tang W., Chi Y... Zhang X.: An ortho-substituted BIPHEP ligand and its applications in Rh-catalyzed hydrogenation of cyclic enamides, Org. Lett. 2002, 4, 1695.
• 36. a) Hopkins J. M., Dalrymple S. A., Parvez M., Keay B. A.: 3,3'-disubstituted BINAP ligands: synthesis, resolution, and applications in asymmetric hydrogenation. Org. Lett. 2005, 7, 3765; b) Rankic D. A., Lucciola D., Keay B. A.: Application of 3,3'-Disubstituted xylBINAP Derivatives in Inter- and Intramolecular Asymmetric Heck/Mizoroki Reactions. Tetrahedon Lett. 2010, 51, 5724; c) Wu S., He M., Zhang X.: Synthesis of ortho-phenyl substituted MeO-BIPHEP ligand and its application in Rh-catalyzed asymmetric hydrogenation. Tetrahedron: Asymmetry 2004, 15, 2177; d) Gorobets E., Sun G., Wheatley B. M. M„ Parvez M., Keay B. A.: Synthesis, Resolution and Applications of3,3'-Bis(RO)-MeO-BIPHEP Derivatives. Tetrahedon Lett. 2004,45, 3597; e) Hopkins J. M., Gorobets E., Sun G., Wheatley B. M. M., Parvez M., Keay B. A.: Applications of 3,3'-Disubstituted BINAP Derivatives in Inter- and Intramolecular Heck/Mizoroki Reactions. Synlett 2006, 18,3120.
• 37. Benincori T., Cesarotti E., Piccolo O., Sannicolo F.: 2,2',5,5'-Tetramethy-l-4,4'-bis(diphenylphosphino)-3,3'-bithiophene: A new, very efficient, easily accessible, chiral biheteroaromatic ligand for homogeneous stereoselective catalysis. J. Org. Chem. 2000, 65, 2043.