MCM-41 Supported Chiral Amino Alcohols as Enantioselective Catalysts for the Reduction of Ketones

Mi Sun Whang; Yong Ku Kwon; Geon-Joong Kim

Journal of Industrial and Engineering Chemistry, Vol.8, No.3, 262-267, May, 2002

Export Citation

MCM-41 Supported Chiral Amino Alcohols as Enantioselective Catalysts for the Reduction of Ketones

Mi Sun Whang, Yong Ku Kwon¹, and Geon-Joong Kim^†

Department of Chemical Engineering, Inha University, Incheon 402-751, Korea
¹Department of Polymer Science and Engineering, Inha University, Incheon 402-751, Korea

E-mail:

The introduction of functional organic groups onto the mesoporous walls has been performed through the co-condensation of siloxanes and organosiloxane precursors during MCM-formation by solvent evaporation method using C(16)TMACl surfactant as a template. The organo-functionalized mesoporous materials were used to immobilize the chiral ligands and MCM-41-supported amino alcohols were prepared to use as asymmetric catalysts for reduction of aromatic ketones. The results were compared with those obtained using unsupported amino alcohols. Higher enantioselectivity was achieved on the MCM-41-supported amino alcohols than silica gel-supported ones.

Keywords:asymmetric reduction;ketone;MCM-41;amino alcohol;enantioselectivity

[References]

Weigel LO, Tetrahedron Lett., 31, 7101 (1990)
Noyori R, Tomino I, Tanimoto Y, Nishizawa M, J. Am. Chem. Soc., 106, 6709 (1984)
Brown HC, Park WS, Cho BT, Ramachandran PV, J. Org. Chem., 52, 5406 (1987)
Itsuno S, Hirao A, Nakshama S, Yamazaki N, J. Chem. Soc.-Perkin Trans. 1, 1673 (1983)
Itsuno S, Nakano M, Miyazaki K, Masuda H, Ito K, Mhizao A, Nakahama S, J. Chem. Soc.-Perkin Trans. 1, 2039 (1985)
Corey EJ, Bakshi RK, Shibata S, J. Am. Chem. Soc., 109, 5551 (1987)
Corey EJ, Bakshi RK, Shibata S, J. Org. Chem., 53, 2861 (1988)
Mehler T, Martens J, Tetrahedron: Asymmetry, 4, 2299 (1993)
Itsuno S, Nakano M, Ito K, Hirao A, Owa M, Kanda N, Nakahama S, J. Chem. Soc.-Perkin Trans. 1, 2615 (1985)
Hermkens PHH, Ottenheijm HCJ, Rees DC, Tetrahedron, 53, 5643 (1997)
Soai K, Watanabe M, Yamamoto A, J. Org. Chem., 55, 4832 (1990)
Soai K, Niwa S, Watanabe M, J. Chem. Soc.-Perkin Trans. 1, 109 (1989)
Giffels G, Beliczey J, Felder M, Kragel U, Tetrahedron: Asymmetry, 9, 691 (1998)
Kim GJ, Shin JH, Tetrahedron Lett., 40, 6827 (1999)
Kim SH, Ong HJ, Chung ST, Jin MJ, J. Ind. Eng. Chem., 7(4), 259 (2001)
Kim SW, Bae SJ, Hyeon T, Kim BM, Microporous Mesoporous Mater., 44, 523 (2001)
Bellocq N, Brunel D, Lasperas M, Moreau P, Stud. Surf. Sci. Catal., 108, 485 (1997)
Lin HP, Yang LY, Mou CY, Liu SB, Lee HK, New J. Chem., 24, 253 (2000)
Tsuji K, Jones CW, Davis ME, Microporous Mesoporous Mater., 29, 339 (1999)
Brunel JM, Maffei M, Buono G, Tetrahedron: Asymmetry, 5, 2255 (1993)

[Referenced By]

[Related Articles]

[1] Weigel LO, Tetrahedron Lett., 31, 7101 (1990)

[2] Noyori R, Tomino I, Tanimoto Y, Nishizawa M, J. Am. Chem. Soc., 106, 6709 (1984)

[3] Brown HC, Park WS, Cho BT, Ramachandran PV, J. Org. Chem., 52, 5406 (1987)

[4] Itsuno S, Hirao A, Nakshama S, Yamazaki N, J. Chem. Soc.-Perkin Trans. 1, 1673 (1983)

[5] Itsuno S, Nakano M, Miyazaki K, Masuda H, Ito K, Mhizao A, Nakahama S, J. Chem. Soc.-Perkin Trans. 1, 2039 (1985)

[6] Corey EJ, Bakshi RK, Shibata S, J. Am. Chem. Soc., 109, 5551 (1987)

[7] Corey EJ, Bakshi RK, Shibata S, J. Org. Chem., 53, 2861 (1988)

[8] Mehler T, Martens J, Tetrahedron: Asymmetry, 4, 2299 (1993)

[9] Itsuno S, Nakano M, Ito K, Hirao A, Owa M, Kanda N, Nakahama S, J. Chem. Soc.-Perkin Trans. 1, 2615 (1985)

[10] Hermkens PHH, Ottenheijm HCJ, Rees DC, Tetrahedron, 53, 5643 (1997)

[11] Soai K, Watanabe M, Yamamoto A, J. Org. Chem., 55, 4832 (1990)

[12] Soai K, Niwa S, Watanabe M, J. Chem. Soc.-Perkin Trans. 1, 109 (1989)

[13] Giffels G, Beliczey J, Felder M, Kragel U, Tetrahedron: Asymmetry, 9, 691 (1998)

[14] Kim GJ, Shin JH, Tetrahedron Lett., 40, 6827 (1999)

[15] Kim SH, Ong HJ, Chung ST, Jin MJ, J. Ind. Eng. Chem., 7(4), 259 (2001)

[16] Kim SW, Bae SJ, Hyeon T, Kim BM, Microporous Mesoporous Mater., 44, 523 (2001)

[17] Bellocq N, Brunel D, Lasperas M, Moreau P, Stud. Surf. Sci. Catal., 108, 485 (1997)

[18] Lin HP, Yang LY, Mou CY, Liu SB, Lee HK, New J. Chem., 24, 253 (2000)

[19] Tsuji K, Jones CW, Davis ME, Microporous Mesoporous Mater., 29, 339 (1999)

[20] Brunel JM, Maffei M, Buono G, Tetrahedron: Asymmetry, 5, 2255 (1993)