Chiral Calix[4]arenes-Bearing Prolinamide Functionality as Organocatalyst for Asymmetric Direct Aldol Reactions in Water

References

• Lindstorm, U. M. Organic Reactions in Water (Blackwell Publishing: Oxford, 2007).
   Google Scholar
• Kobayashi, S. and K. Manabe. “Development of Novel Lewis Acid Catalysts for Selective Organic Reactions in Aqueous Media.” Acc. Chem. Res. 35 (2002): 209–17.
   PubMed Web of Science ®Google Scholar
• Lindstrom, U. M. “Stereoselective Organic Reactions in Water.” Chem. Rev. 102 (2002): 2751–72.
   PubMed Web of Science ®Google Scholar
• Paradowska, J., M. Stodulski, and J. Mlynarski. “Catalysts Based on Amino Acids for Asymmetric Reactions in Water.” Angew. Chem., Int. Ed. 48 (2009): 4288–4297.
   PubMed Web of Science ®Google Scholar
• Raj, M., and K. Singh. “Organocatalytic Reactions in Water.” Chem. Commun. (2009): 6687–703.
   PubMedGoogle Scholar
• Akceylan, E., A. Uyanik, S. Eymur, O. Sahin, and M. Yilmaz. “Calixarene-proline Functionalized Iron Oxide Magnetite Nanoparticles(Calix-Pro-MN): An Efficient Recyclable Organocatalyst for Asymmetric Aldol Reaction in Water.” Appl. Catal. A 499 (2015): 205–12.
   Web of Science ®Google Scholar
• Bhowmick, S., and K. C. Bhowmick. “Catalytic Asymmetric Carbon-Carbon Bond-Forming Reactions in Aqueous Media.” Tetrahedron: Asym. 22 (2011): 1945–79.
   Web of Science ®Google Scholar
• Li, C. J. “Organic Reactions in Aqueous Media with a Focus on C-C Bond Formations: A Decade Update.” Chem. Rev. 105 (2005): 3095–165.
   PubMed Web of Science ®Google Scholar
• List, B., A. R. Lerner, and C. F.Barbas III“Proline-Catalyzed Direct Asymmetric Aldol Reactions.” J. Am. Chem. Soc. 122 (2000): 2395–6.
   Web of Science ®Google Scholar
• Dalko, P. L., and L. Moisan. “In the Golden Age of Organocatalysis.” Angew. Chem. Int. Ed. 43 (2004): 5138–75.
   PubMed Web of Science ®Google Scholar
• Seayad, J., and B. List. “Asymmetric Organocatalysis.” Org. Biomol. Chem. 3 (2005): 719–24.
   PubMed Web of Science ®Google Scholar
• List, B. “The Ying and Yang of Asymmetric Aminocatalysis.” Chem Commun. (2006): 819–24.
   PubMed Web of Science ®Google Scholar
• Mase, N., and C. F. Barbas III “In Water, on Water, and by Water: Mimicking Nature's Aldolases with Organocatalysis and Water.” Org. Biomol. Chem. 8 (2010): 4043–50.
   PubMed Web of Science ®Google Scholar
• Mase, N., Y. Nakai, N. Ohara, H. Yoda, K. Takabe, F. Tanaka, and C. F. Barbas III “Organocatalytic Direct Asymmetric Aldol Reactions in Water.” J. Am. Chem. Soc. 128 (2006): 734–5.
   PubMed Web of Science ®Google Scholar
• Huang, J., X. Zhang, and D. Armstrong. “Highly Efficient Asymmetric Direct Stoichiometric Aldol Reactions on/in Water.” Angew. Chem., Int. Ed. 46 (2007): 9073–7.
   PubMed Web of Science ®Google Scholar
• Giacalone, F., M. Gruttadauria, P. Agrigento, P. L. Meo, and R. Noto. “Advances towards Highly Active and Stereoselective Simple and Cheap Proline-Based Organocatalysts.” Eur. J. Org. Chem. (2010): 5696–704.
   Web of Science ®Google Scholar
• Raj, M., and V. K. Singh. “Organocatalytic Reactions in Water.” Chem. Commun. (2009): 6687–6703.
   PubMedGoogle Scholar
• Giacalone, F., M. Gruttadauria, P. L. Meo, S. Riela, and R. Notoa. “New Simple Hydrophobic Proline Derivatives as Highly Active and Stereoselective Catalysts for the Direct Asymmetric Aldol Reaction in Aqueous Medium.” Adv. Synth. Catal. 350 (2008): 2747–60.
   Web of Science ®Google Scholar
• An, Y. J., Y. X. Zhang, Y. Wua, Z. M. Liu, C. Pi, and J. C. Tao. “Simple Amphiphilic Isosteviol–Proline Conjugates as Chiral Catalysts for the Direct Asymmetric Aldol Reaction in the Presence Of Water.” Tetrahedron: Asym. 21 (2010): 688–94.
   Web of Science ®Google Scholar
• Hea, T., K. Li, M. Y. Wua, M. B. Wub, N. Wang, L. Pua, and X. Q. Yua. “Water Promoted Enantioselective Aldol Reaction by Proline-Cholesterol and -Diosgenin Based Amphiphilic Organocatalysts.” Tetrahedron 69 (2013): 5136–43.
   Web of Science ®Google Scholar
• Doyaguez, E. Y., and A. F. Mayoralas. “Proline–Cyclodextrin Conjugates: Synthesis and Evaluation as Catalysts for Aldol Reaction in Water.” Tetrahedron 68 (2012): 7345–54.
   Web of Science ®Google Scholar
• Triandafillidi, I., A. Bisticha, E. Voutyritsa, Galiatsatou, G., and C. G. Kokotos. “tert-Butyl ester or benzylamide of the dipeptide Pro-Gly as Organocatalysts for the Asymmetric Aldol Reaction.” Tetrahedron 71 (2015): 932–40.
   Web of Science ®Google Scholar
• Psarra, A., C. G. Kokotos, and P. Moutevelis-Minakakis. “tert-Butyl esters of tripeptides based on Pro-Phe as Organocatalysts for the Asymmetric Aldol Reaction in Aqueous or Organic Medium.” Tetrahedron 70 (2014): 608–15.
   Web of Science ®Google Scholar
• Jia, Y.-N., F.-C. Wu, X. Ma, G.-J. Zhu, and C.-S. Da. “Highly Efficient Prolinamide-Based Organocatalysts for the Direct Asymmetric Aldol Reaction in Brine.” Tetrahedron 50 (2009): 3059–62.
   Web of Science ®Google Scholar
• Monge-Marcet, A., R. Pleixats, X. Cattoen, M. W. C. Man, D. A. Alonso, C. Najerac. “Prolinamide Bridged Silsesquioxane as an Efficient, Eco-Compatible and Recyclable Chiral Organocatalysts.” New. J. Chem. 35 (2011): 2766–72.
   Web of Science ®Google Scholar
• Guana, Z., Y. Luo, B.-Q. Zhang, K. Heinen, D.-C. Yang, and Y.-H. He. “The Application of a Structurally Simple, Recyclable, and Large-Scale L-Prolinamide Catalyst for Asymmetric Aldol Reactions.” Tetrahedron: Asym. 25 (2014): 802–12.
   Web of Science ®Google Scholar
• Mase, N., Y. Nakai, N. Ohara, H. Yoda, K. Takabe, F. Tanaka, and C. F. Barbas III “Organocatalytic Direct Asymmetric Aldol Reactions in Water.” J. Am. Chem. Soc. 128 (2006): 734–5.
   PubMed Web of Science ®Google Scholar
• Hayashi, Y., T. Sumiya, J. Takahashi, H. Gotoh, T. Urushima, and M. Shoji. “Highly Diastereo and Enantioselective Direct Aldol Reactions in Water.” Angew. Chem., Int. Ed. 45 (2006): 958–61.
   PubMed Web of Science ®Google Scholar
• Mase, N., K. Watanabe, H. Yoda, K. Takabe, F. Tanaka, and C. F. Barbas III “Organocatalytic Direct Michael Reaction of Ketones and Aldehydes with beta-nitrostyrene in Brine.” J. Am. Chem. Soc. 128 (2006): 4966–7.
   PubMed Web of Science ®Google Scholar
• Hayashi, Y., S. Aratake, T. Okano, J. Takahashi, T. Sumiya, and M. Shoji. “Combined Proline-Surfactant Organocatalyst for the Highly Diastereo- and Enantioselective Aqueous Direct Cross-Aldol Reaction of Aldehydes.” Angew. Chem., Int. Ed. 45 (2006): 5527–9.
   PubMed Web of Science ®Google Scholar
• Vicens, J., J. Harrowfield, and L. Backlouti. In Calixarenes in the Nanoworld (Dordrecht, The Netherlands : Springer, 2007).
   Google Scholar
• Elcin, S., and H. Deligoz. “Di-substituted azocalix[4]arenes containing Chromogenic Groups: Synthesis, Characterization, Extraction, and Thermal Behavior.” Tetrahedron 69 (2013): 6832–8.
   Web of Science ®Google Scholar
• Joseph, R., and C. P. Rao. “Ion and Molecular Recognition by Lower Rim 1,3-Di-conjugates of Calix[4]arene as Receptors.” Chem. Rev. 111 (2011): 4658–702.
   PubMed Web of Science ®Google Scholar
• Neri, P., Sessler, J. L., and M.-X. Wang. Calixarenes and Beyond. (Switzerland, Springer International Publishing, 2016).
   Google Scholar
• Asfari, Z., V. Bohmer, J. Harrowfield, and J. Vicens. Calixarenes 2001 (Dordrecht, The Netherlands: Kluwer Academic, 2001).
   Google Scholar
• Qazi, M. A., I. Qureshi, and S. Memon. “A Highly Copper Selective Chromogenic calix [4] Arene Derivative.” New J. Chem. 34 (2010): 2579–86.
   Web of Science ®Google Scholar
• Yilmaz, M., and S. Erdemir. “Calixarene-based Receptors for Molecular Recognition.” Turk. J. Chem. 37 (2013): 558–85.
   Web of Science ®Google Scholar
• Gutsche, C. D. Calixarenes An Introduction, 2nd ed. (Cambridge, UK : The Royal Society of Chemistry, Thomas Graham House, 2008).
   Google Scholar
• Li, Z. Y., J. W. Chen, L. Wang, and Y. Pan“Highly Enantioselective Direct Aldol Reactions Catalyzed by Proline Derivatives Based on a Calix[4]arene Scaffold in the Presence of Water.” Synlett (2009): 2356–81.
   Web of Science ®Google Scholar
• Li, Z. Y., J. W. Chen, Y. Liu, W. Xia, and L. Wang. “The Use of Calixarenes Inasymmetric Catalysis.” Curr. Org. Chem. 15 (2011): 39–61.
   Web of Science ®Google Scholar
• Eymur, S., E. Akceylan, O. Sahin, A. Uyanik, and M. Yilmaz. “Direct Enantioselective Aldol Reactions Catalyzed by calix[4]arene-based L-proline Derivatives in the Water.” Tetrahedron 70 (2014): 4471–7.
   Web of Science ®Google Scholar
• Uyanik, A., M. Bayrakci, S. Eymur, and M. Yilmaz. “Upper rim-Functionalized calix[4]arene-based L-proline as Organocatalyst for Direct Asymmetric Aldol Reactions in Water and Organic Media.” Tetrahedron 70 (2014): 9307–13.
   Web of Science ®Google Scholar
• Xu, Z. X., G. K. Li, C. F. Chen, and Z. T. Huang. “Inherently chiral calix[4]arene-based Bifunctional Organocatalysts for Enantioselective Aldol Reactions.” Tetrahedron 64 (2008): 8668–75.
   Web of Science ®Google Scholar
• D'Elia, V., H. Zwicknagl, and O. Reiser. “Short alpha/beta-peptides as Catalysts for Intra- and Intermolecular Aldol Reactions.” J. Org. Chem. 73 (2008): 3262–5.
   PubMed Web of Science ®Google Scholar
• Chen, F., S. Huang, H. Zhang, F. Liu, and Y. Peng. “Proline-based dipeptides with two amide units as Organocatalyst for the Asymmetric Aldol Reaction of Cyclohexanone with Aldehydes.” Tetrahedron 64 (2008): 9585–91.
   Web of Science ®Google Scholar
• Maya, V., M. Raj, and V. K. Singh. “Highly Enantioselective Organocatalytic Direct Aldol Reaction in an Aqueous Medium.” Org. Lett. 9 (2007): 2593–395.
   PubMed Web of Science ®Google Scholar
• Fu, S. D., X. K. Fu, S. P. Zhang, X. C. Zou, and X. J. Wu. “Highly diastereo- and enantioselective direct aldol reactions by 4-tert-butyldimethylsiloxy-substituted Organocatalysts Derived from N-prolylsulfonamides in Water.” Tetrahedron: Asym. 20 (2009): 2390–6.
   Web of Science ®Google Scholar
• Collins, M., M. A. McKervey, E. Madigan, M. B. Moran, M. Owens, G. Ferguson, and S. J. Harris. “Chemically Modified calix[4]arenes, Regioselective Synthesis of 1,3-(distal) Derivatives and Related Compounds. X-ray Crystal Structure of a diphenoldinitrile.” J. Chem. Soc. Perkin. Trans. 1 (1991): 3137–42.
   Google Scholar
• Chawla, H. M., N. Pant, B. Srivastava, and S. Upreti. “Convenient Direct Synthesis of Bisformylated Calix[4]arenes via Ipso Substitution.” Org. Lett. 8 (2006): 2237–40.
   PubMed Web of Science ®Google Scholar
• Hoang, L., S. Bahmanyar, K. N. Houk, and B. List. “Kinetic and stereochemical Evidence for the Involvement of Only One Proline Molecule in the Transition States of proline-catalyzed intra- and intermolecular aldol reactions.” J. Am. Chem. Soc. 125 (2003): 16–7.
   PubMed Web of Science ®Google Scholar
• Bahmanyar, S., K. N. Houk, H. J. Martin, and B. List. “Quantum Mechanical Predictions of the Stereoselectivities of proline-Catalyzed Asymmetric Intermolecular aldol reactions.” J. Am. Chem. Soc. 125 (2003): 2475–9.
   PubMed Web of Science ®Google Scholar