Abstract
Metal-catalyzed enantioselective transfer reduction of ketones to enantiomerically enriched chiral alcohols has recently attracted attention. Therefore, a series of methyl alkyl or alkyl/aryl ketones have been reduced by using Ru(II), Rh(I) and Ir(III) catalysts based on C 2-symmetric chiral ferrocenyl phosphinite ligands. The corresponding optically active secondary alcohols were obtained in excellent conversions and moderate-to-good enantioselectivities. The best results were obtained with an iridium catalyst, giving up to 98% conversion and 80% ee.
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Malacea R, Poli R, Manoury E (2010) Coord Chem Rev 254:729
Wang Z, Ding K, Uozumi Y, Ding K, Uozumi Y (eds) (2008) Handbook of asymmetric heteregeneous catalysis. Wiley-VCH, Weinheim, p 1
Elma D, Durap F, Aydemir M, Baysal A, Meric N, Ak B, Turgut Y, Gümgüm B (2013) J Organomet Chem 729:46
Abdur-Rashid K, Faatz M, Lough AJ, Morris RH (2001) J Am Chem Soc 123:7473
Wang X-B, Zhou Y-G (2008) J Org Chem 73:5640
Jayasinghe D, Kraatz H-B (2006) Inorg Chim Acta 359:3054
Guo R, Elpett C, Chen X, Song D, Morris RH (2005) Chem Commun 24:3050
Balakrishna MS, Rao S, Choubey B (2012) J Chem Sci 124:1191
Aydemir M, Baysal A, Ozkar S, Yıldırım LT (2011) Inorg Chim Acta 367:166
Ok F, Aydemir M, Durap F, Baysal A (2014) Appl Organomet Chem 28:38
Adhikary A, Guan HR (2015) ACS Catal 5:6858
Toma S, Csizmadiova J, Meciarova M, Sebesta R (2014) Dalton Trans 43:16557
Zhu D-Y, Chen P, Xia J-B (2016) ChemCatChem 8:68–73
Rafikova K, Kystaubayeva N, Aydemir M, Kayan C, Ocak YS, Temel H, Zazybin A, Gurbuz N, Ozdemir I (2014) J Organomet Chem 758:1
Arrayas RG, Adrio J, Carretero JC (2006) Angew Chem Int Ed 45:7674
Sutcliffe OB, Bryce MR (2003) Tetrahedron Asymmetry 14:2297
Blaser HA, Spindler F (1997) Chimia 51:297
Burk MJ, Gross MF (1994) Tetrahedron Lett 35:9363
Kang J, Lee JH, Ahn SH, Choi JS (1998) Tetrahedron Lett 39:5523
Sawamura M, Kuwano R, Ito Y (1994) Angew Chem Int Ed Engl 33:111
Sawamura M, Ito Y (1992) Chem Rev 92:857
Kılıç A, Durap F, Aydemir M, Baysal A, Taş E (2008) J Organomet Chem 693(17):2835
Song J-H, Cho D-J, Jeon S-J, Kim Y-H, Kim T-J (1999) Inorg Chem 38:89
Patti A, Pedotti S (2003) Tetrahedron Asymmetry 14:597
Galka PW, Kraatz H-B (2003) J Organomet Chem 674:24
Aydemir M, Durap F, Baysal A, Meric N, Buldağ A, Gümgüm B, Özkar S, Yıldırım LT (2010) J Mol Catal A Chem 326:75
Durap F, Aydemir M, Baysal A, Elma D, Ak B, Turgut Y (2014) Inorg Chim Acta 411:77
Ak B, Aydemir M, Ocak YS, Durap F, Kayan C, Baysal A, Temel H (2014) Inorg Chim Acta 409:244
Ak B, Elma D, Meric N, Kayan C, Işık U, Aydemir M, Durap F, Baysal A (2015) Tetrahedron Asymmetry 20:1257
Ak B, Elma D, Meriç N, Kayan C, Işık U, Aydemir M, Durap F, Baysal A (2013) Tetrahedron Asymmetry 24:1257
Alvarez M, Lugan N, Mathieu R (1994) J Chem Soc Dalton Trans 2755. doi:10.1039/DT9940002755
Gao JX, Ikariya T, Noyori R (1996) Organometallics 15:1087
Kuroki Y, Asada D, Sakamaki Y, Iseki K (2000) Org Lett 41:4603
Ak B, Durap F, Aydemir M, Baysal A (2015) Appl Organomet Chem 29:764
Ak B, Aydemir M, Durap F, Meriç N, Baysal A (2015) Inorg Chim Acta 438:42
Ak B, Aydemir M, Durap F, Meriç N, Elma D, Baysal A (2015) Tetrahedron: Asymmetry 26:1307
Yamakawa M, Yamada I, Noyori R (2001) Angew Chem Int Ed 40:2818
Durap F, Elma Karakaş D, Ak B, Baysal A, Aydemir M (2016) J Organomet Chem 818:92
Acknowledgements
Partial supports of this work by TUBİTAK (Project Number: 111T419) and Dicle University (Project Numbers: FEN.16.010 (NMR), DÜBAP FEN.15.021 and FEN.15.022) are gratefully acknowledged.
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Baysal, A., Elma Karakaş, D., Meriç, N. et al. Chiral phosphinites as efficient ligands for enantioselective Ru(II), Rh(I) and Ir(III)-catalyzed transfer hydrogenation reactions. Transit Met Chem 42, 365–372 (2017). https://doi.org/10.1007/s11243-017-0140-1
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DOI: https://doi.org/10.1007/s11243-017-0140-1