Enantioselective Addition of Diethylzinc to Aldehydes Catalyzed by MCM-41-Supported Ephedrine

Sang-Han Kim; Ho-Joon Ong; Sung-Taik Chung; Myung-Jong Jin

Journal of Industrial and Engineering Chemistry, Vol.7, No.4, 259-261, July, 2001

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Enantioselective Addition of Diethylzinc to Aldehydes Catalyzed by MCM-41-Supported Ephedrine

Sang-Han Kim, Ho-Joon Ong, Sung-Taik Chung, and Myung-Jong Jin^†

School of Chemical Science & Engineering, Inha University, Inchon 402-751, Korea

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MCM-41 silica-supported ephedrine was prepared and utilized as an asymmetric catalyst for enantioselective addition of diethylzinc reagent to aldehyde. The MCM-supported ephedrine led to much faster reaction and higher asymmetric induction than silica gel-supported ephedrine. Highly ordered MCM-41 silica was found to be better inorganic support for the catalytic system than amorphous silica gel.

Keywords:MCV-41 silica-supported ephedrine;asymmetric catalyst;enantioselective addition

[References]

Noyori R, in Asymmetric Catalysis in Organic Synthesis, Wiley-Interscience, New York (1994)
Noyori R, Kitamura M, Angew. Chem.-Int. Edit., 30, 49 (1991)
Soai K, Niwa S, Chem. Rev., 92, 833 (1992)
Hodge P, Sherrington DC, in Polymer-Supported Reactions in Organic Synthesis, Wiley, New York (1980)
Smith K, Solid Supports and Catalysts in Organic Synthesis, Ellis Horwood and Prentice Hall, New York (1992)
Hermkens PHH, Ottenheijm HCJ, Rees DC, Tetrahedron, 53, 5643 (1997)
Bhalay G, Dunstan A, Glen A, Synlett, 12, 1846 (2000)
Itsuno S, Frechet JMJ, J. Org. Chem., 52, 4140 (1987)
Watanabe M, Soai K, J. Chem. Soc.-Perkin Trans. 1, 837 (1994)
Soai K, Watanabe M, Yamamoto A, J. Org. Chem., 55, 4832 (1990)
Heckel A, Seebach D, Angew. Chem.-Int. Edit., 39, 163 (2000)
Seller H, Seebach D, Angew. Chem.-Int. Edit., 38, 1918 (1999)
Sutra P, Brunel D, Chem. Commun., 2485 (1996)
Liu CH, Yu WY, J. Org. Chem., 63, 7364 (1998)
Choi HJ, Cho MS, Kang KK, Ahn WS, Microporous Mesoporous Mater., 39, 19 (2000)
Sung-Suh HM, Kim DS, Park SE, J. Ind. Eng. Chem., 5(3), 191 (1999)
Jeong HS, Jeong SY, Lee JM, Yim DJ, Ryu SK, J. Ind. Eng. Chem., 5(4), 247 (1999)
Ryoo R, Jun S, J. Phys. Chem. B, 101(3), 317 (1997)
Soai K, Niwa S, Chem. Rev., 92, 833 (1992)
Kang J, Kim JW, Lee JW, Kim DS, Kim JL, Bull. Korean Chem. Soc., 17, 1135 (1996)
Ramon DJ, Yus M, Tetrahedron: Asymmetry, 8, 2479 (1997)
Sola L, Reddy KS, Vidal-Ferran A, Moyano A, Perica MA, Riera A, Alvarez-Larena A, Piniella J, J. Org. Chem., 63, 7078 (1998)
Kim SH, Chung ST, Jin MJ, J. Ind. Eng. Chem., 4(4), 345 (1998)
Paleo MR, Cabeza I, Sardina J, J. Org. Chem., 65, 2108 (2000)
Vanppen DLA, De Vos DE, Genet MJ, Rouxhlet PG, Jacobs PA, Angew. Chem.-Int. Edit., 34, 560 (1995)
Chalone P, Perera R, Tetrahedron Lett., 26, 3013 (1987)

[Referenced By]

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[1] Noyori R, in Asymmetric Catalysis in Organic Synthesis, Wiley-Interscience, New York (1994)

[2] Noyori R, Kitamura M, Angew. Chem.-Int. Edit., 30, 49 (1991)

[3] Soai K, Niwa S, Chem. Rev., 92, 833 (1992)

[4] Hodge P, Sherrington DC, in Polymer-Supported Reactions in Organic Synthesis, Wiley, New York (1980)

[5] Smith K, Solid Supports and Catalysts in Organic Synthesis, Ellis Horwood and Prentice Hall, New York (1992)

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

[7] Bhalay G, Dunstan A, Glen A, Synlett, 12, 1846 (2000)

[8] Itsuno S, Frechet JMJ, J. Org. Chem., 52, 4140 (1987)

[9] Watanabe M, Soai K, J. Chem. Soc.-Perkin Trans. 1, 837 (1994)

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

[11] Heckel A, Seebach D, Angew. Chem.-Int. Edit., 39, 163 (2000)

[12] Seller H, Seebach D, Angew. Chem.-Int. Edit., 38, 1918 (1999)

[13] Sutra P, Brunel D, Chem. Commun., 2485 (1996)

[14] Liu CH, Yu WY, J. Org. Chem., 63, 7364 (1998)

[15] Choi HJ, Cho MS, Kang KK, Ahn WS, Microporous Mesoporous Mater., 39, 19 (2000)

[16] Sung-Suh HM, Kim DS, Park SE, J. Ind. Eng. Chem., 5(3), 191 (1999)

[17] Jeong HS, Jeong SY, Lee JM, Yim DJ, Ryu SK, J. Ind. Eng. Chem., 5(4), 247 (1999)

[18] Ryoo R, Jun S, J. Phys. Chem. B, 101(3), 317 (1997)

[19] Soai K, Niwa S, Chem. Rev., 92, 833 (1992)

[20] Kang J, Kim JW, Lee JW, Kim DS, Kim JL, Bull. Korean Chem. Soc., 17, 1135 (1996)

[21] Ramon DJ, Yus M, Tetrahedron: Asymmetry, 8, 2479 (1997)

[22] Sola L, Reddy KS, Vidal-Ferran A, Moyano A, Perica MA, Riera A, Alvarez-Larena A, Piniella J, J. Org. Chem., 63, 7078 (1998)

[23] Kim SH, Chung ST, Jin MJ, J. Ind. Eng. Chem., 4(4), 345 (1998)

[24] Paleo MR, Cabeza I, Sardina J, J. Org. Chem., 65, 2108 (2000)

[25] Vanppen DLA, De Vos DE, Genet MJ, Rouxhlet PG, Jacobs PA, Angew. Chem.-Int. Edit., 34, 560 (1995)

[26] Chalone P, Perera R, Tetrahedron Lett., 26, 3013 (1987)