Full Paper
Asymmetric modular synthesis of cylindrically chiral FerroPHOS ligands for the Rh-catalyzed asymmetric hydroboration
Jahyo Kang,
Jun Hee Lee,
Jin Bum Kim,
Gi Jeong Kim,
Corresponding Author
Jahyo Kang
Department of Chemistry, Sogang University, Shinsudong 1, Mapoku, Seoul 121-742, Republic of Korea
Department of Chemistry, Sogang University, Shinsudong 1, Mapoku, Seoul 121-742, Republic of KoreaSearch for more papers by this authorJun Hee Lee
Department of Chemistry, Sogang University, Shinsudong 1, Mapoku, Seoul 121-742, Republic of Korea
Search for more papers by this authorJin Bum Kim
Department of Chemistry, Sogang University, Shinsudong 1, Mapoku, Seoul 121-742, Republic of Korea
Search for more papers by this authorGi Jeong Kim
Department of Chemistry, Sogang University, Shinsudong 1, Mapoku, Seoul 121-742, Republic of Korea
Search for more papers by this authorJahyo Kang,
Jun Hee Lee,
Jin Bum Kim,
Gi Jeong Kim,
Corresponding Author
Jahyo Kang
Department of Chemistry, Sogang University, Shinsudong 1, Mapoku, Seoul 121-742, Republic of Korea
Department of Chemistry, Sogang University, Shinsudong 1, Mapoku, Seoul 121-742, Republic of KoreaSearch for more papers by this authorJun Hee Lee
Department of Chemistry, Sogang University, Shinsudong 1, Mapoku, Seoul 121-742, Republic of Korea
Search for more papers by this authorJin Bum Kim
Department of Chemistry, Sogang University, Shinsudong 1, Mapoku, Seoul 121-742, Republic of Korea
Search for more papers by this authorGi Jeong Kim
Department of Chemistry, Sogang University, Shinsudong 1, Mapoku, Seoul 121-742, Republic of Korea
Search for more papers by this authorFirst published: 19 May 2000
Citations: 25
Abstract
Asymmetric modular synthesis of air-stable ferrocenyl bisphosphine ligands with cylindrical chirality was achieved employing asymmetric catalytic methods and these chiral ligands were screened in asymmetric hydroboration reaction. Chirality 12:378–382, 2000. © 2000 Wiley-Liss, Inc.
LITERATURE CITED
- 1Noyori R. Asymmetric catalysis in organic synthesis. New York: John Wiley & Sons, Inc.; 1994.
- 2Marquarding D, Klusaek H, Gokel G, Hoffmann P, Ugi I. Correlation of central and planar chirality in ferrocene derivatives. J Org Chem 1970; 35: 5389–5393.
- 3 A Togni, T Hayashi, eds. Ferrocenes. Weinheim: VCH; 1995.
- 4a) Mgarrity J, Spindler F, Fuchs R, Eyer M. Assymetric hydrogenation of furolimidazol derivatives. Eur. Pat. Appl. EP. 624587 A2, Chem Abstr. 122:P81369q.
b) Borman S. Ferrocene derivatives find use as chiral catalysts. Chem Eng News 1996; 22: 38–40.
10.1021/cen-v074n009.p038 Google Scholar
- 5Miyashita A, Yasuda A, Takaya H, Toriumi T, Ito T, Souchi T, Noyori R. Synthesis of 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP), an atropisomeric chiral bis(triaryl)phosphine, and its use in the rhodium(I)-catalyzed asymmetric hydrogenation of α-(acylamino)acrylic acids. J Am Chem Soc 1980; 102: 7932–7934.
- 6Kang J, Lee JH, Ahn SH, Choi JS. Asymmetric synthesis of a new cylindrically chiral and air-stable ferrocenyldiphosphine and its application to rhodium-catalyzed hydrogenation. Tetrahedron Lett 1998; 39: 5523–5526.
- 7Kang J, Lee JW, Kim JI. Enantioselective addition of diethylzinc to α-branched aldehydes. Chem Commun 1994: 2009–2010. b) Kang J, Kim DS, Kim JI. Enantioselective addition of diethylzinc to aldehydes catalyzed by a drug-unrelated chiral amino thiol and the corresponding disulfide. Synlett, 1994: 842–844. c) Kang J, Kim JW, Lee JW, Kim DS, Kim JI. Chiral β-amino thiol catalysts for the enantioselective addition of diethylzinc to aldehydes. Bull Korean Chem Soc 1996; 17: 1135–1142.
- 8a) Almena Perea JJ, Börner A, Knochel P. A versatile modular approach to new chiral C2-symmetrical ferrocenyl ligands: highly enantioselective Rh-catalyzed hydrogenation of α-acetamidoacrylic acid derivatives. Tetrahedron Lett 1998; 39: 8073–8076.
10.1016/S0040-4039(98)01832-2 Google Scholarb) Almena Perea JJ, Lotz M, Knochel P. Synthesis and application of C2-symmetrical diamino FERRIPHOS as ligands for enantioselective Rh-catalyzed preparation of chiral α-acetamidoacrylic acids. Tetrahedron: Asymmetry 1999; 10: 375–384.10.1016/S0957-4166(99)00002-6 Google Scholar
- 9a) Schwink L, Knochel P. Enantioselective preparation of C2-symmetrical ferrocenyl ligands for asymmetric catalysis. Chem Eur J 1998; 4: 950–968. b) ibid. A new practical asymmetric synthesis of C2-symmetrical 1,1′-ferrocenyl diols via CBS-reduction. Tetrahedron Lett 1996; 37: 25–28. c) Corey EJ, Shibata S, Bakshi RK. An efficient and catalytically enantioselective route to (S)-(−)-phenyloxirane. J Org Chem 1998; 53: 2861–2863.
- 10Green M, Kuc TA, Taylor SH. Cationic transition-metal complexes, Part I. Synthesis and reactions of bis(diene)-rhodium and -iridium tetrafluoroborates. J Chem Soc (A) 1971; 2334–2337.
- 11Armarego WLF, Perrin DD. Purification of laboratory chemicals, 4th edition. Oxford: Butterworth-Heinemann, 1996.
- 12Still WC, Kahn M, Mitra A. Rapid chromatographic technique for preparative separations with moderate resolution. J Org Chem 1978; 43: 2923–2925.
- 13The diamino ferrocenylbisphosphine 4b is already known and can be prepared by a resolutional method; see Hayashi T, Yamamoto A, Hojo M, Kishi K, Ito Y, Nishioka E, Miura H, Yanagi KJ. Organomet Chem 1989; 370: 129–139.
- 14a) Hayashi T, Mise T, Fukushima M, Kagotani M, Nagashima N, Hamada Y, Matsumoto A, Kwakami S, Konishi M, Yamamoto K, Kumada M. Asymmetric synthesis catalyzed by chiral ferrocenylphosphine-transition metal complexes. I. Preparation of chiral ferrocenylphosphines. Bull Chem Soc Jpn 1980; 53: 1138–1151. b) Hayashi T, Yamazaki A. Asymmetric synthesis catalyzed by chiral ferrocenylphosphine-transition metal complexes. IX. Preparation of chiral ferrocenylphosphines containing an aminoalkyl side chain. J Organomet Chem 1991; 413: 295–302.
- 15a) Brown DS, Ley SV. Direct substitution of 2-benzenesulphonyl cyclic ethers using organozinc reagents. Tetrahedron Lett 1988; 29: 4869–4872. b) Okamoto Y, Yoshioka K, Yamana T, Mori H. Palladium-catalyzed cross-coupling of bromobenzenes, containing an acetyl or a formyl group, with organozinc reagents. J Organomet Chem 1989; 369: 285–290. c) Almena Perea JJ, Ireland T, Knochel P. Substitution of ferrocenyl acetates with organozinc reagents. An enantioselective preparation of polyfunctional chiral ferrocenes. Tetrahedron Lett 1997; 38: 5961–5964.
- 16a) Hayashi T, Matsumoto Y, Ito Y. Catalytic asymmetric hydroboration of styrenes. J Am Chem Soc 1989; 111: 3426–3428. b) Hayashi T, Matsumoto Y, Ito Y. Asymmetric hydroboration of styrenes catalyzed by cationic chiral phosphine-rhodium(I) complexes. Tetrahedron: Asymmetry 1991; 2: 601–612. c) Schnyder A, Togni A, Wiesli U. Electronic effects in asymmetric catalysis. Synthesis and structure of model rhodium complexes containing ferrocenyl ligands for use in the hydroboration reaction. Organometallics 1997; 16: 255–260. d) Son SU, Jang H-Y, Lee IS, Chung YK. Synthesis of planar chiral (1,2-disubstituted arene)chromium tricarbonyl compounds and their application in asymmetric hydroboration. Organometallics 1998; 17: 3236–3239.
