Abstract
Chiral (salen)Mn(III) complexes were immobilized into mesoporous helical silica for asymmetric epoxidation of unfunctionalized alkenes, and chiral synergistic effects between supporting material and (salen)Mn(III) were investigated. Characterization revealed both carriers and supported catalysts had a hierarchical structure composed of morphology and internal channels. Supporting materials had helical morphology and excessive left-handed channels, while most supported catalysts still had excessive left-handed channels although their morphology might degrade. Catalysis revealed the synergistic effects between mesoscopic and molecular chirality exist, and the combination of left-handed channels with (R,R)-(salen)Mn(III) appeared to be more enantioselective than that with (S,S)-salen counterpart in epoxidation of terminal and cyclic alkenes.
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Wurst JM, Liu G, Tan DS (2011) J Am Chem Soc 133:7916–7925
Cho H, Katoh S, Sayama S, Murakami K, Nakanishi H, Kajimoto Y, Ueno H, Kawasaki H, Aisaka K, Uchida I (1996) J Med Chem 39:3797–3805
Ottenbacher RV, Samsonenko DG, Talsi EP, Bryliakov KP (2014) ACS Catal 4:1599–1606
Katsuki T, Sharpless KB (1980) J Am Chem Soc 102:5974–5976
Jacobsen EN, Zhang W, Güler ML (1991) J Am Chem Soc 113:6703–6704
Irie R, Noda K, Ito Y, Katsuki T (1991) Tetrahedron Lett 32:1055–1058
Zulauf A, Mellah M, Hong X, Schulz E (2010) J Chem Soc Dalton Trans 39:6911–6935
Xia QH, Ge HQ, Ye CP, Liu ZM, Su KX (2005) Chem Rev 105:1603–1662
Pozzi G, Cinato F (1998) Chem Commun 877–878
Kureshy RI, Roy T, Khan NH, Abdi SHR, Sadhukhan A, Bajaj HC (2012) J Catal 286:41–50
Tan R, Yin D, Yu N, Tao L, Fu Z, Yin D (2006) J Mol Catal A 259:125–132
Bu J, Judeh ZMA, Ching CB, Kawi S (2003) Catal Lett 85:183–187
Bhattacharjee S, Anderson JA (2004) Chem Commun 554–555
Choudary BM, Ramani T, Maheswaran H, Prashant L, Ranganath KVS, Kumar KV (2006) Adv Synth Catal 348:493–498
Zhang H, Zhang Y, Li C (2006) J Catal 238:369–381
Yu K, Gu Z, Ji R, Lou L, Liu S (2009) Tetrahedron 65:305–311
Song CE, Lee S (2002) Chem Rev 102:3495–3524
Hoffmann F, Cornelius M, Morell J, Fröba M (2006) Angew Chem Int Ed 45:3216–3251
Che S, Liu Z, Ohsuna T, Sakamoto K, Terasaki O, Tatsumi T (2004) Nature 429:281–284
Shang Y, Li Y, He X, Du S, Zhang L, Shi E, Wu S, Li Z, Li P, Wei J, Wang K, Zhu H, Wu D, Cao A (2013) ACS Nano 7:1446–1453
Yang S, Zhao L, Yu C, Zhou X, Tang J, Yuan P, Chen D, Zhao D (2006) J Am Chem Soc 128:10460–10466
Snir Y, Kamien RD (2005) Science 307:1067
Yamamoto T, Yamada T, Nagata Y, Suginome M (2010) J Am Chem Soc 132:7899–7901
Fernandes CI, Saraiva MS, Nunes TG, Vaz PD, Nunes CD (2014) J Catal 309:21–32
Han Y, Zhao L, Ying JY (2007) Adv Mater 19:2454–2459
Yu K, Gu Z, Ji R, Lou L, Ding F, Zhang C, Liu S (2007) J Catal 252:312–320
Zhang Z, Guan F, Huang X, Wang Y, Sun Y (2012) J Mol Catal A 363–364:343–353
Piaggio P, Langham C, McMorn P, Bethell D, Bulman-Page PC, Hancock FE, Sly C, Hutchings GJ (2000) J Chem Soc Perkin Trans 2:143–148
Guo Z, Du Y, Chen Y, Ng SC, Yang Y (2010) J Phys Chem C 114:14353–14361
Zhang H, Xiang S, Xiao J, Li C (2005) J Mol Catal A 238:175–184
Canali L, Cowan E, Deleuze H, Gibson CL, Sherrington DC (2000) J Chem Soc Perkin Trans 1:2055–2066
Sing KSW, Everett DH, Haul RAW, Moscou L, Pierotti RA, Rouquérol J, Siemieniewska T (1985) Pure Appl Chem 57:603–619
Ohsuna T, Liu Z, Che S, Terasaki O (2005) Small 1:233–237
Galarneau A, Nader M, Guenneau F, Renzo FD, Gedeon A (2007) J Phys Chem C 111:8268–8277
Zhang W, Loebach JL, Wilson SR, Jacobsen EN (1990) J Am Chem Soc 112:2801–2803
Malek K, Li C, van Santen RA (2007) J Mol Catal A 271:98–104
Das P, Kuźniarska-Biernacka I, Silva AR, Carvalho AP, Pires J, Freire C (2006) J Mol Catal A 248:135–143
Palucki M, Pospisil PJ, Zhang W, Jacobsen EN (1994) J Am Chem Soc 116:9333–9334
Yu K, Lou L, Lai C, Wang S, Ding F, Liu S (2006) Catal Commun 7:1057–1060
Song CE, Roh EJ (2000) Chem Commun 837-838
Li X, Shen Q, Zhang G, Zhang D, Zheng A, Guan F, Sun Y (2013) Catal Commun 41:126–131
Xu Z, Ma X, Ma Y, Wang Q, Zhou J (2009) Catal Commun 10:1261–1266
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This work was supported by Shaanxi Higher Education Teaching Reform Project (No. 13BY02, Cultivation of Creative Ability of Scientific Research for the Undergraduate). This work was supported by the Fundamental Research Funds for the Central Universities (No. xjj2014005).
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Zhang, J., Li, L., Li, Y. et al. Immobilization of Chiral (salen)Manganese(III) Complexes Into Mesoporous Helical Silica for Asymmetric Epoxidation of Alkenes. Catal Lett 145, 1148–1161 (2015). https://doi.org/10.1007/s10562-015-1510-y
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DOI: https://doi.org/10.1007/s10562-015-1510-y