Stereoselective Aldol Reaction in Aqueous Solution Using Prolinamido-Glycosides as Water-Compatible Organocatalyst
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http://www.scirp.org/journal/PaperInformation.aspx?PaperID=53042#.VLSJdcnQrzE
ABSTRACT
Prolinamido-glycoside
catalyzed asymmetric aldol reaction in aqueous media is reported. The
reactions are rapid and highly stereoselective when water is used as
solvent. The stereoselectivities were under influence of configurations
of a prolyl residue of the catalyst and α-chiral aldehydes. Water
soluble prolinamido-glycoside catalysts are easily separable from
reaction mixture and can be recycled and re-used several times.
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References
Miura,
D. and Machinami, T. (2015) Stereoselective Aldol Reaction in Aqueous
Solution Using Prolinamido-Glycosides as Water-Compatible
Organocatalyst. Modern Research in Catalysis, 4, 20-27. doi: 10.4236/mrc.2015.41003.
| [1] | Tanaka, F. and Barbas, C.F. (2007) Enantioselective Organocatalysis, Reactions and Experimental Procedures. In: Dalko, P.I., Ed., Weiley-VCH, Weinheim, 19-55. |
| [2] | List,
B., Lerner, R.A. and Barbas III, C.F. (2000) Proline-Catalyzed Direct
Asymmetric Aldol Reactions. Journal of the American Chemical Society,
122, 2395-2396. http://pubs.acs.org/doi/abs/10.1021/ja994280y http://dx.doi.org/10.1021/ja994280y |
| [3] | Sakthivel,
K., Not, W., Bui, T. and Barbas III, C.F. (2001) Amino Acid Catalyzed
Direct Asymmetric Aldol Reactions: A Bioorganic Approach to Catalytic
Asymmetric Carbon-Carbon Bond-Forming Reactions. Journal of the American
Chemical Society, 123, 5260-5267. http://pubs.acs.org/doi/abs/10.1021/ja010037z |
| [4] | Dickerson,
T.J. and Janda, K.D. (2002), Aqueous Aldol Catalysis by a Nicotine
Metabolite. Journal of the American Chemical Society, 124, 3220-3221.
http://pubs.acs.org/doi/pdf/10.1021/ja017774f http://dx.doi.org/10.1021/ja017774f |
| [5] | Dickerson,
T.J., Lovell, T., Meijler, M.M., Noodleman, L. and Janda, K.D.
(2004)Nornicotine Aqueous Aldol Reactions: Synthetic and Theoretical
Investigations into the Origins of Catalysis. The Journal of Organic
Chemistry, 69, 6603-6609. http://pubs.acs.org/doi/abs/10.1021/jo048894j http://dx.doi.org/10.1021/jo048894j |
| [6] | Pedatella,
S., De Nisco, M., Mastroianni, D., Naviglio, D., Nucci, A. and Caputo,
R. (2011) Diastereo- and Enantioselective Direct Aldol Reactions in
Aqueous Medium: A New Highly Efficient Proline-Sugar Chimeric Catalys,
Advanced Synthesis & Catalysis, 353, 1443-1446. http://onlinelibrary.wiley.com/doi/10.1002/adsc.201100143/abstract http://dx.doi.org/10.1002/adsc.201100143 |
| [7] | Burroughs,
L., Vale, M.E., Gilks, J.A., Forintos, H., Hayes, C.J. and Clarke, P.A.
(2010) Efficient Asymmetric Organocatalytic Formation of Erythrose and
Threose under Aqueous Conditions. Chemical Communications, 46,
4776-4778. http://pubs.rsc.org/en/content/articlelanding/2010/cc/c0cc00613k#!divAbstract http://dx.doi.org/10.1039/c0cc00613k |
| [8] | Maya, V., Raj, M. and Singh, V.K. (2007) Highly Enantioselective Organocatalytic Direct Aldol Reaction in an Aqueous Medium. Organic Letters, 9, 2593-2595. http://dx.doi.org/10.1021/ol071013l |
| [9] | Ramasastry,
S.S.V., Albertshofer, K., Utsumi, N. and Barbas III, C.F. (2008)
Water-Compatible Organocatalysts for Direct Asymmetric syn-Aldol
Reactions of Dihydroxyacetone and Aldehydes. Organic Letters, 10,
1621-1624. http://pubs.acs.org/doi/abs/10.1021/ol8002833 |
| [10] | Kofoed,
J., Reymond, J.-L. and Darbre, T. (2005) Prebiotic Carbohydrate
Synthesis: Zinc-Proline Catalyzes Direct Aqueous Aldol Reactions of
α-Hydroxy Aldehydes and Ketones. Organic & Biomolecular Chemistry,
3, 1850-1855. http://pubs.rsc.org/en/content/articlelanding/2005/ob/b501512j#!divAbstract |
| [11] | Tsutsui,
A., Takeda, H., Kimura, M., Fujimoto, T. and Machinami, T. (2007) Novel
Enantiocontrol System with Aminoacyl Derivatives of Glucoside as
Enamine-Based Organocatalysts for Aldol Reaction in Aqueous Media.
Tetrahedron Letters, 48, 5213-5217. http://www.sciencedirect.com/science/article/pii/S0040403907010350 |
| [12] | Miura,
D., Fujimoto, T., Tsutsui, A. and Machinami, T. (2013) Stereoselective
Synthesis of Ketoses by Aldol Reaction Using Water-Compatible
Prolinamide Catalysts in Aqueous Media. Synlett, 24, 1501-1504. https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0033-1339197 |
| [13] | Suami, T. (1982) Nitrosourea derivatives, Fr, Demande, Fr 2493318, A1, 19820507. |
| [14] | Jeffs,
P.W., Chan, G., Sitrin, R., Holder, N., Roberts, G.D. and DeBrosse, C.
(1985) The Structure of Glycolipid Components of the Aridicin Antibiotic
Complex. The Journal of Organic Chemistry, 50, 1726-1731. http://pubs.acs.org/doi/abs/10.1021/jo00210a030 http://dx.doi.org/10.1021/jo00210a030 |
| [15] | Schimd,
C.R., Bryant, J.D., Dowlatzedah, M., Phillips, J.L., Prather, D.E.,
Schantz, R.D., Sear, N.L. and Vianco, C.S. (1991) Synthesis of
2,3-O-isopropylidene-D-glyceraldehyde in High Chemical and Optical
Purity: Observations on the Development of a Practical Bulk Process. The
Journal of Organic Chemistry, 56, 4056-4058. http://pubs.acs.org/doi/abs/10.1021/jo00012a049 http://dx.doi.org/10.1021/jo00012a049 |
| [16] | Wilde,
H.D., Clercq, P.D. and Vandewalle, M. (1987) L-(S)-erythrulose a Novel
Precursor to L-2,3-O-isopropylidene- C3 Chirons. Tetrahedron Letters,
28, 4757-4758. http://dx.doi.org/10.1016/S0040-4039(00)96618-8 http://www.sciencedirect.com/science/article/pii/S0040403900966188 |
| [17] | Forbes,
D.C., Ene, D.G. and Doyle, M.P. (1998) Stereoselective Synthesis of
Substituted 5-Hydroxy-1,3-dioxanes. Synthesis, 6, 879-882. https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-1998-2090 http://dx.doi.org/10.1055/s-1998-2090 |
| [18] | West,
B.F., Bhat, K.V. and Zorbach, W.W. (1968) 2-Deoxy Sugars Part XIII.
1,3-Dideoxy-d-erythro-hexulose. Carbohydrate Research, 8, 253-261. http://www.sciencedirect.com/science/article/pii/S0008621500822302 http://dx.doi.org/10.1016/S0008-6215(00)82230-2 |
| [19] | Kito,
Y., Kawakishi, S. and Namiki, M. (1980) A Novel Reaction of Sugars with
Anion Radical of Carbon Dioxide Produced from Formate. Agricultural and
Biological Chemistry, 44, 2695-2701. https://www.jstage.jst.go.jp/article/bbb1961/44/11/44_11_2695/_article http://dx.doi.org/10.1271/bbb1961.44.2695 |
| [20] | Torsell, K.B.G., Hazell, A.C. and Hazell, R.G. (1985) Silylnitronates and NITRILE Oxides in Organic Synthesis. A Novel Route to D,L-deoxysugars. Use of Aluminum Oxide as Solid Phase Base for generation of. Tetrahedron, 41, 5569-5575. http://www.sciencedirect.com/science/article/pii/S0040402001913584 |
| [21] | Iwamoto, H., Yoshida, M., Yamamoto, M. and Tanuma, T. (1984) European Patent Applications, EP 123444A1 19841031. |
| [22] | Tamura, T., Iwamoto, H., Yoshida, M. and Yamamoto, M. (1985) Japanese Kokai Tokkyo Koho, JP60172996 A19850906. |
| [23] | Majewski,
M. and Nowak, P.J. (2000) Aldol Addition of Lithium and Boron Enolates
of 1,3-Dioxan-5-ones to Aldehydes. A New Entry into Monosaccharide
Derivatives. The Journal of Organic Chemistry, 65, 5152-5160. http://pubs.acs.org/doi/abs/10.1021/jo0002238 http://dx.doi.org/10.1021/jo0002238 |
| [24] | Majewski,
M. and Nowak, P. (1999) Stereoselective Synthesis of Protected
Ketohexoses via Aldol Reaction of Chiral Dioxanone Enolate. Synlett, 9,
1447-1449. http://dx.doi.org/10.1055/s-1999-2862 https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-1999-2862 |
| [25] | Grondal,
C. and Enders, D. (2006) Direct Asymmetric Organocatalytic de Novo
Synthesis of Carbohydrates. Tetrahedron, 62, 329-337. http://www.sciencedirect.com/science/article/pii/S0040402005016522 http://dx.doi.org/10.1016/j.tet.2005.09.060 |
| [26] | Suri,
J.T., Mitsumori, S., Albertshofer, K., Tanaka, F. and Barbas III, C.F.
(2006) Dihydroxyacetone Variants in the Organocatalytic Construction of
Carbohydrates: Mimicking Tagatose and Fuculose Aldolases. The Journal of
Organic Chemistry, 71, 3822-3828. http://pubs.acs.org/doi/abs/10.1021/jo0602017 http://dx.doi.org/10.1021/jo0602017 |
| [27] | Hann,
R.M., Tilden, E.B. and Hudson, C.S.J. (1938) The Oxidation of Sugar
Alcohols by Acetobacter suboxydans. Journal of the American Chemical
Society, 60, 1201-1203. http://pubs.acs.org/doi/abs/10.1021/ja01272a058 http://dx.doi.org/10.1021/ja01272a058 |
| [28] | Hochster,
R.M. and Watson, R.W. (1953) XYLOSE ISOMERASE. Journal of the American
Chemical Society, 75, 3284-3285.
http://pubs.acs.org/doi/abs/10.1021/ja01109a516 http://dx.doi.org/10.1021/ja01109a516 |
| [29] | Bean,
R.C. and Hassid, W.Z.J. (1955) Synthesis of Disaccharides with Pea
Preparations. Journal of the American Chemical Society, 77, 5737-5738.
http://pubs.acs.org/doi/abs/10.1021/ja01626a081 http://dx.doi.org/10.1021/ja01626a081 |
| [30] | Hollmann,
S. and Touster, O. (1956) An Enzymatic Pathway from L-Xylulose to
D-Xylulose. Journal of the American Chemical Society, 78, 3544-3545.
http://pubs.acs.org/doi/abs/10.1021/ja01595a080 http://dx.doi.org/10.1021/ja01595a080 |
| [31] | Suzuki, K., Yuki, Y. and Mukaiyama, T. (1981) The Stereoselective Synthesis of D-Ribulose. Chemistry Letters, 11, 1529-1532. https://www.jstage.jst.go.jp/article/cl1972/10/11/10_11_1529/_article http://dx.doi.org/10.1246/cl.1981.1529 |
| [32] | Drueckhammer,
D.G., Durrwachter, J.R., Pederson, R.L., Richard, L., Crans, D.C.,
Daniels, L. and Wong, C.H. (1989) Reversible and in Situ Formation of
Organic Arsenates and Vanadates as Organic Phosphate Mimics in Enzymatic
Reactions: Mechanistic Investigation of Aldol Reactions and Synthetic
Applications. The Journal of Organic Chemistry, 54, 70-77. http://pubs.acs.org/doi/abs/10.1021/jo00262a021 |
| [33] | Vuorien,
T. and Serianni, A.S. (1991) Synthesis of D-erythro-2-pentulose and
D-threo-2-pentulose and Analysis of the 13C- and 1H-n.m.r. Spectra of
the 1-13C- and 2-13C-Substituted Sugars. Carbohydrate Research, 209,
13-31. http://www.sciencedirect.com/science/article/pii/000862159180142A http://dx.doi.org/10.1016/0008-6215(91)80142-A |
| [34] | Fisher,
M., Kaehling, H. and Schmid, W. (2011) Gram Scale Synthesis of
3-Fluoro-1-hydroxyacetone Phosphate: A Novel Donor Substrate in Rabbit
Muscle Aldolase-Catalyzed Aldol Reactions. Chemical Communications, 47,
6647- 6649. http://pubs.rsc.org/en/content/articlelanding/2011/cc/c1cc11579k#!divAbstract http://dx.doi.org/10.1039/c1cc11579k eww150113lx |
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