Progress on proline derivatives as organocatalysts

ZHAO Ming-zhu; JIANG Zhi-hui; CAI Zhan; ZHANG Da-zhi

doi:10.3969/j.issn.1006-0111.2012.01.005

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Volume 30 Issue 1

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Article Navigation > Journal of Pharmaceutical Practice and Service > 2012 > 30(1): 19-24,41

ZHAO Ming-zhu, JIANG Zhi-hui, CAI Zhan, ZHANG Da-zhi. Progress on proline derivatives as organocatalysts[J]. Journal of Pharmaceutical Practice and Service, 2012, 30(1): 19-24,41. doi: 10.3969/j.issn.1006-0111.2012.01.005

Citation:

ZHAO Ming-zhu, JIANG Zhi-hui, CAI Zhan, ZHANG Da-zhi. Progress on proline derivatives as organocatalysts[J]. Journal of Pharmaceutical Practice and Service, 2012, 30(1): 19-24,41. doi: 10.3969/j.issn.1006-0111.2012.01.005

Progress on proline derivatives as organocatalysts

doi: 10.3969/j.issn.1006-0111.2012.01.005

Department of Organic Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China

Received Date: 2011-01-20
Rev Recd Date: 2011-05-20

Abstract

The small organic molecules catalyst was a hotspot in asymmetric synthesis. Due to the excellent enantiselectivity of proline in many asymmetric reactions, people showed great interest in the modification of it, which aimed to get better organocatalysts. Proline derivatives were divided into ten kinds and reviewed the progression in asymmetric reactions according to these types in this paper.
- proline derivatives,
- asymmetric synthesis,
- enantioselectivity,
- organocatalysis

References

[1]	Yan ZY, Niu YN, Wei HL, et al. Combining proline and 'click chemistry': a class of versatile organocatalysts for the highly diastereo-and enantioselective Michael addition in water[J]. Tetrahedron: Asymmetry, 2006, 17: 3288.
[2]	Zhang L, Xu H, Mi XL, et al. Chiral pyrrolidine-azole conjugates: Simple and efficient asymmetric organocatalysts for Michael addition to nitrostyrenes[J]. Chinese Sci Bull, 2010, 55: 1735.
[3]	Saito S, Nakadai M, Yamamoto H. Diamine-protonic acid catalysts for catalytic asymmetric aldol reaction[J]. Synlett, 2001, 8: 1245.
[4]	Nobuyuki M, Yusuke N, Naoko O, et al. Organocatalytic direct asymmetric aldol reactions in water[J]. J Am Chem Soc, 2006, 128: 734.
[5]	Pansare SV, Raie LK. Secondary-secondary diamine catalysts for the enantioselective michael addition of cyclic ketones to nitroalkenes[J]. Tetrahedron, 2009, 65: 4557.
[6]	Marigo M, Fielenbach D, Braunton A, et al. Enantioselective formation of stereogenic carbon-fluorine centers by a simple catalytic method[J]. Angew Chem Int Ed, 2005, 44: 3703.
[7]	Wu J, Ni B, Headley AD. Di(methylimidazole)prolinol silyl ether catalyzed highly michael addition of aldehydes to nitroolefins in water[J]. Org Lett, 2009, 11: 3354.
[8]	Lin QY, Meloni D, Pan YC, Michael Xia, et al. Enantioselective synthesis of Janus kinase inhibitor INCB018424 via an organocatalytic aza-michael reaction[J]. Org Lett, 2009, 11: 1999.
[9]	Bondzic PB, Urushima T, Ishikawa H, et al. Asymmetric epoxidation of α-substituted acroleins catalyzed by diphenylprolinol silyl ether[J]. Org Lett, 2010, 12: 5434.
[10]	Jia YN, Wu FC, Ma X, et al. Highly ef?cient prolinamide-based organocatalysts for the direct asymmetric aldol reaction in brine[J]. Tetrahedron Lett, 2009, 50: 3059.
[11]	Pasternak M, Paradowska J, Rogozińska M, et al. Direct asymmetric α-hydroxymethylation of ketones in homogeneous aqueous solvents[J]. Tetrahedron Lett, 2010, 51: 4088.
[12]	林国强, 陈耀全, 李月明, 等. 手性合成-不对称反应及其应用[M]. 北京: 科学出版社,2007: 118.
[13]	Saha S, Seth S, Moorthy JN. Functionalized proline with double hydrogen bonding potential: highly enantioselective michael addition of carbonyl compounds to b-nitrostyrenes in brine[J]. Tetrahedron Lett, 2010, 51: 5281.
[14]	Yang H, Mahapatra S, Cheong PHY, et al. Highly stereoselective and scalable anti-aldol reactions using N-(p-Dodecylphenylsulfonyl)-2-pyrrolidinecarboxamide: scope and rigins of stereoselectivities[J]. J Org Chem, 2010, 75:7279.
[15]	Wei SW, Yalalov DA, Tsogoeva SB, et al. New highly enantioselective thiourea-based bifunctional organocatalysts for nitro-michael addition reactions[J]. Catalysis Today, 2007, 121: 151.
[16]	Demir AS, Eymur S. Self-assembly of organocatalysts for the enantioselective michael addition of aldehydes to nitroalkenes[J]. Tetrahedron:Asymmetry, 2010, 21: 112.
[17]	Lu AD, Gao P, Wu Y, et al. Highly enantio-and diastereoselective michael addition of cyclohexanone to nitroolefins catalyzed by a chiral glucose-based bifunctional secondary amine-thiourea catalyst[J]. Org Biomol Chem, 2009, 7: 3141.
[18]	Tsogoeva SB, Jagtap SB, Ardemasova ZA, et al. Ardemasovab 4-trans-Amino-proline based di-and tetrapeptides as organic catalysts for asymmetric C-C bond formation reactions[J]. Tetrahedron: Asymmetry, 2006, 17: 989.
[19]	Chen FB, Huang S, Zhang H, et al. Proline-based dipeptides with two amide units as organocatalyst for the asymmetric aldol reaction of cyclohexanone with aldehydes[J]. Tetrahedron, 2008, 64: 9585.
[20]	Wu FC, Da CS, Du ZX, et al. N-Primary-Amine-Terminal γ-Turn tetrapeptides as organocatalysts for highly enantioselective aldol reaction[J]. J Org Chem, 2009, 74: 4812.
[21]	Agarwal J, Peddinti RK. Asymmetric michael addition catalysed by sugar-based prolinamides in solvent-free conditions[J]. Tetrahedron Lett, 2011, 52: 117.
[22]	Dinér P, Amedjkouh M. Aminophosphonates as organocatalysts in the direct asymmetric aldol reaction: towards syn selectivity in the presence of Lewis bases[J]. Org Biomol Chem, 2006, 4: 2091.
[23]	Tan B, Zeng XF, Lu Y, et al. Rational design of organocatalyst: highly stereoselective michael addition of cyclic ketones to nitroole?ns[J]. Org Lett, 2009, 11: 1927.
[24]	Xu DZ, Liu YJ, Hui Li, et al. A new kind of organophosphorus compounds as an efficient catalyst for asymmetric C-C bond formation reactions[J]. Tetrahedron, 2010, 66: 8899.
[25]	Luo S, Mi X, Zhang L, et al. Functionalized chiral Ionic Liquids as highly efficient asymmetric organocatalysts for michael addition to nitroolefins[J]. Angew Chem Int Ed, 2006, 45: 3093.
[26]	Xu DZ, Liu YJ, Shi S, et al. Chiral quaternary alkylammonium ionic liquid ［Pro-dabco]BF4］: as a recyclable and highly efficient organocatalyst for asymmetric michael addition reactions[J]. Tetrahedron: Asymmetry, 2010, 21: 2530.
[27]	Fu YQ, An YJ, Liu WM, et al. Highly diastereo-and enantioselective direct aldol reaction catalyzed by simple amphiphilic proline derivatives[J]. Catal Lett, 2008, 124: 397.
[28]	Kristensen TE, Kristian V, Jakobsen MG, et al. A general approach for preparation of polymer-supported chiral organocatalysts via acrylic copolymerization[J]. J Org Chem, 2010, 75: 1620.
[29]	Prasetyanto EA, Khan NH, Seo HU, et al. Asymmetric epoxidation of a, b-unsaturated ketones over heterogenized chiral proline diamide complex catalyst in the solvent-Free condition[J]. Top Catal, 2010, 53: 1381.

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通讯作者: 陈斌, bchen63@163.com

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沈阳化工大学材料科学与工程学院沈阳 110142

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Progress on proline derivatives as organocatalysts

Department of Organic Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, China

Received Date: 2011-01-20

Rev Recd Date: 2011-05-20

Key words:

Abstract: The small organic molecules catalyst was a hotspot in asymmetric synthesis. Due to the excellent enantiselectivity of proline in many asymmetric reactions, people showed great interest in the modification of it, which aimed to get better organocatalysts. Proline derivatives were divided into ten kinds and reviewed the progression in asymmetric reactions according to these types in this paper.

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Reference (29)

[1]	Yan ZY, Niu YN, Wei HL, et al. Combining proline and 'click chemistry': a class of versatile organocatalysts for the highly diastereo-and enantioselective Michael addition in water[J]. Tetrahedron: Asymmetry, 2006, 17: 3288.
[2]	Zhang L, Xu H, Mi XL, et al. Chiral pyrrolidine-azole conjugates: Simple and efficient asymmetric organocatalysts for Michael addition to nitrostyrenes[J]. Chinese Sci Bull, 2010, 55: 1735.
[3]	Saito S, Nakadai M, Yamamoto H. Diamine-protonic acid catalysts for catalytic asymmetric aldol reaction[J]. Synlett, 2001, 8: 1245.
[4]	Nobuyuki M, Yusuke N, Naoko O, et al. Organocatalytic direct asymmetric aldol reactions in water[J]. J Am Chem Soc, 2006, 128: 734.
[5]	Pansare SV, Raie LK. Secondary-secondary diamine catalysts for the enantioselective michael addition of cyclic ketones to nitroalkenes[J]. Tetrahedron, 2009, 65: 4557.
[6]	Marigo M, Fielenbach D, Braunton A, et al. Enantioselective formation of stereogenic carbon-fluorine centers by a simple catalytic method[J]. Angew Chem Int Ed, 2005, 44: 3703.
[7]	Wu J, Ni B, Headley AD. Di(methylimidazole)prolinol silyl ether catalyzed highly michael addition of aldehydes to nitroolefins in water[J]. Org Lett, 2009, 11: 3354.
[8]	Lin QY, Meloni D, Pan YC, Michael Xia, et al. Enantioselective synthesis of Janus kinase inhibitor INCB018424 via an organocatalytic aza-michael reaction[J]. Org Lett, 2009, 11: 1999.
[9]	Bondzic PB, Urushima T, Ishikawa H, et al. Asymmetric epoxidation of α-substituted acroleins catalyzed by diphenylprolinol silyl ether[J]. Org Lett, 2010, 12: 5434.
[10]	Jia YN, Wu FC, Ma X, et al. Highly ef?cient prolinamide-based organocatalysts for the direct asymmetric aldol reaction in brine[J]. Tetrahedron Lett, 2009, 50: 3059.
[11]	Pasternak M, Paradowska J, Rogozińska M, et al. Direct asymmetric α-hydroxymethylation of ketones in homogeneous aqueous solvents[J]. Tetrahedron Lett, 2010, 51: 4088.
[12]	林国强, 陈耀全, 李月明, 等. 手性合成-不对称反应及其应用[M]. 北京: 科学出版社,2007: 118.
[13]	Saha S, Seth S, Moorthy JN. Functionalized proline with double hydrogen bonding potential: highly enantioselective michael addition of carbonyl compounds to b-nitrostyrenes in brine[J]. Tetrahedron Lett, 2010, 51: 5281.
[14]	Yang H, Mahapatra S, Cheong PHY, et al. Highly stereoselective and scalable anti-aldol reactions using N-(p-Dodecylphenylsulfonyl)-2-pyrrolidinecarboxamide: scope and rigins of stereoselectivities[J]. J Org Chem, 2010, 75:7279.
[15]	Wei SW, Yalalov DA, Tsogoeva SB, et al. New highly enantioselective thiourea-based bifunctional organocatalysts for nitro-michael addition reactions[J]. Catalysis Today, 2007, 121: 151.
[16]	Demir AS, Eymur S. Self-assembly of organocatalysts for the enantioselective michael addition of aldehydes to nitroalkenes[J]. Tetrahedron:Asymmetry, 2010, 21: 112.
[17]	Lu AD, Gao P, Wu Y, et al. Highly enantio-and diastereoselective michael addition of cyclohexanone to nitroolefins catalyzed by a chiral glucose-based bifunctional secondary amine-thiourea catalyst[J]. Org Biomol Chem, 2009, 7: 3141.
[18]	Tsogoeva SB, Jagtap SB, Ardemasova ZA, et al. Ardemasovab 4-trans-Amino-proline based di-and tetrapeptides as organic catalysts for asymmetric C-C bond formation reactions[J]. Tetrahedron: Asymmetry, 2006, 17: 989.
[19]	Chen FB, Huang S, Zhang H, et al. Proline-based dipeptides with two amide units as organocatalyst for the asymmetric aldol reaction of cyclohexanone with aldehydes[J]. Tetrahedron, 2008, 64: 9585.
[20]	Wu FC, Da CS, Du ZX, et al. N-Primary-Amine-Terminal γ-Turn tetrapeptides as organocatalysts for highly enantioselective aldol reaction[J]. J Org Chem, 2009, 74: 4812.
[21]	Agarwal J, Peddinti RK. Asymmetric michael addition catalysed by sugar-based prolinamides in solvent-free conditions[J]. Tetrahedron Lett, 2011, 52: 117.
[22]	Dinér P, Amedjkouh M. Aminophosphonates as organocatalysts in the direct asymmetric aldol reaction: towards syn selectivity in the presence of Lewis bases[J]. Org Biomol Chem, 2006, 4: 2091.
[23]	Tan B, Zeng XF, Lu Y, et al. Rational design of organocatalyst: highly stereoselective michael addition of cyclic ketones to nitroole?ns[J]. Org Lett, 2009, 11: 1927.
[24]	Xu DZ, Liu YJ, Hui Li, et al. A new kind of organophosphorus compounds as an efficient catalyst for asymmetric C-C bond formation reactions[J]. Tetrahedron, 2010, 66: 8899.
[25]	Luo S, Mi X, Zhang L, et al. Functionalized chiral Ionic Liquids as highly efficient asymmetric organocatalysts for michael addition to nitroolefins[J]. Angew Chem Int Ed, 2006, 45: 3093.
[26]	Xu DZ, Liu YJ, Shi S, et al. Chiral quaternary alkylammonium ionic liquid ［Pro-dabco]BF4］: as a recyclable and highly efficient organocatalyst for asymmetric michael addition reactions[J]. Tetrahedron: Asymmetry, 2010, 21: 2530.
[27]	Fu YQ, An YJ, Liu WM, et al. Highly diastereo-and enantioselective direct aldol reaction catalyzed by simple amphiphilic proline derivatives[J]. Catal Lett, 2008, 124: 397.
[28]	Kristensen TE, Kristian V, Jakobsen MG, et al. A general approach for preparation of polymer-supported chiral organocatalysts via acrylic copolymerization[J]. J Org Chem, 2010, 75: 1620.
[29]	Prasetyanto EA, Khan NH, Seo HU, et al. Asymmetric epoxidation of a, b-unsaturated ketones over heterogenized chiral proline diamide complex catalyst in the solvent-Free condition[J]. Top Catal, 2010, 53: 1381.

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Progress on proline derivatives as organocatalysts

doi: 10.3969/j.issn.1006-0111.2012.01.005

Abstract

References

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通讯作者: 陈斌, bchen63@163.com

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