SBA-15 실리카에 고정화된 ruthenium 촉매를 사용한 Microwave하에서의 비대칭 수소 전달반응

진명종; 전인철; Myung-Jong Jin; In-Chul Jun

Korean Chemical Engineering Research, Vol.46, No.4, 752-755, August, 2008

Export Citation

SBA-15 실리카에 고정화된 ruthenium 촉매를 사용한 Microwave하에서의 비대칭 수소 전달반응

Microwave-mediated Asymmetric Hydrogen Transfer by SBA-15-supported Ruthenium Catalyst

진명종 ^†, 전인철¹

인하대학교 화학공학과, 402-751 인천광역시 남구 용현동 253
¹재능대학교 화장품과, 401-714 인천광역시 동구 송림동 122

Myung-Jong Jin^†, and In-Chul Jun¹

Department of Chemical Engineering, Inha University, 253 Yonghyun-dong, Nam-gu, Incheon 402-751, Korea
¹Department of Cosmetics, JaiNeung College, 122 Songlim-dong, Dong-gu, Incheon 401-714, Korea

E-mail:

초록

메조포러스 SBA-15 silica와 (1R,2R)-N-(trimethoxysilylpropyl-N-sulfonyl)-1,2-cyclohaxanediamine 또는 (1R,2R)-N-(trimethoxysilylpropyl- N-sulfonyl)-1,2-diphenylethylenediamine과의 반응을 통하여 메조포러스 silica SBA-15-supported TsCHDA와 TsDPEN가 각각 제조되어졌다. SBA-15-supported TsCHDA로부터 얻어진 ruthenium complex들은 microwave하에서의 케톤의 비대칭 수소 전달반응에서 우수한 촉매능과 만족할 만한 거울상 입체선택도를 주었다. 이 불균일상 SBA-15-supported ruthenium 촉매는 사용이 용이하게 안정할 뿐 만 아니라, 재사용 할 수 있었다. 비대칭 수소전달반응을 위한 microwave를 사용한 효율적인 공정이 개발되었다.

Mesoporous SBA-15 silica-supported TsCHDA and TsDPEN ligands have been prepared by reaction of SBA-15 silica with (1R,2R)- N-(trimethoxysilylpropyl-N-sulfonyl)-1,2-cyclohaxanediamine or (1R,2R)- N-(trimethoxysilylpropyl-N-sulfonyl)-1,2-diphenylethylenediamine-1,2- diphenylethylenediamine, respectively. The Ru complexes exhibited excellent catalytic activity and satisfactory enantioselectivity in the asymmetric hydrogen transfer of ketones under microwave conditions. The heterogeneous Ru catalyst was reusable as well as air-stable to allow easy use. Microwave-assisted efficient procedure has been developed for asymmetric hydrogen transfer.

Keywords:SBA-15;Ru Complex;TsCHDA;Hydrogen Transfer;Microwave

[References]

Zhao DY, Feng JL, Huo QS, Melosh N, Fredrickson GH, Chmelka BF, Stucky GD, Science, 279(5350), 548 (1998)
Sayari A, Han BH, Yang Y, J. Am. Chem. Soc., 126(44), 14348 (2004)
Karimi B, Abedi S, Clark JH, Budarin V, Angew. Chem.-Int. Edit., 45, 4476 (2006)
Leadbeater NE, Marco M, Chem. Rev., 102(10), 3217 (2002)
Raynor SA, Thomas JM, Raja R, Johnson BFG, Bell RG, Mantle MD, Chem. Commun., 1925 (2000)
Johnson BFG, Raynor SA, Shephard DS, Mashmeyer T, Thomas JM, Sankar G, Bromley S, Oldroyd R, Gladden L, Mantle MD, Chem. Commun., 1167 (1999)
Liu PN, Gu PM, Wang F, Tu YQ, Org. Lett., 169 (2004)
Saluzzo C, Halle R, Touchard F, Fache F, Schulz E, Lemaire M, J. Org. Chem., 30-39, 576 (1999)
Hashiguchi S, Fujii A, Takehara J, Ikariya T, Noyori R, J. Am. Chem. Soc., 117(28), 7562 (1995)
Pnterer K, Schwink L, Knochel P, Tetrahedron Lett., 37, 8165 (1996)
Varma RS, Pure Appl. Chem., 73, 193 (2001)
Perreux L, Loupy A, Tetrahedron, 57, 9199 (2001)

[Related Articles]

[1] Zhao DY, Feng JL, Huo QS, Melosh N, Fredrickson GH, Chmelka BF, Stucky GD, Science, 279(5350), 548 (1998)

[2] Sayari A, Han BH, Yang Y, J. Am. Chem. Soc., 126(44), 14348 (2004)

[3] Karimi B, Abedi S, Clark JH, Budarin V, Angew. Chem.-Int. Edit., 45, 4476 (2006)

[4] Leadbeater NE, Marco M, Chem. Rev., 102(10), 3217 (2002)

[5] Raynor SA, Thomas JM, Raja R, Johnson BFG, Bell RG, Mantle MD, Chem. Commun., 1925 (2000)

[6] Johnson BFG, Raynor SA, Shephard DS, Mashmeyer T, Thomas JM, Sankar G, Bromley S, Oldroyd R, Gladden L, Mantle MD, Chem. Commun., 1167 (1999)

[7] Liu PN, Gu PM, Wang F, Tu YQ, Org. Lett., 169 (2004)

[8] Saluzzo C, Halle R, Touchard F, Fache F, Schulz E, Lemaire M, J. Org. Chem., 30-39, 576 (1999)

[9] Hashiguchi S, Fujii A, Takehara J, Ikariya T, Noyori R, J. Am. Chem. Soc., 117(28), 7562 (1995)

[10] Pnterer K, Schwink L, Knochel P, Tetrahedron Lett., 37, 8165 (1996)

[11] Varma RS, Pure Appl. Chem., 73, 193 (2001)

[12] Perreux L, Loupy A, Tetrahedron, 57, 9199 (2001)