Abstract
In the light of growing demand for chiral purity in biological and chemical processes, the synthesis of chiral metal-organic porous materials (CMOPMs) have become immensely important because of their potential applications in chiral separation and asymmetric catalysis. In this chapter, the synthetic strategies for CMOPMs are discussed briefly keeping the focus on their applications. Two distinct approaches have been taken to synthesize a wide variety of chiral structures with different topologies and accessible cavities. Several CMOPMs have shown catalytic activity and enantioselectivity toward a number of chemical transformations. On many occasions, the chiral pores of the MOPMs have been utilized in order to achieve separation of enantiomers from racemates. Recent applications of homochiral MOPMs in heterogeneous, asymmetric catalysis and chiral separations are also presented here.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Abbreviations
- 1,2-pd:
-
1,2-propanediol
- asp:
-
aspartate
- bdc:
-
1,4-benzenedicarboxylate
- BINAP:
-
2,2¢-bis(diphenylphosphino)-1,1¢-binaphthyl
- BINOL:
-
2,2¢-dihydroxy-1,1¢-binaphthyl
- bipy:
-
4,4¢-bipyridine
- bpdc:
-
4,4¢-biphenyldicarboxylate
- bpe:
-
1,2-bis(4-pyridyl)ethylene
- bpy:
-
2,2¢-bipyridine
- btc:
-
1,3,5-benzenetricarboxylate
- CMOPM:
-
Chiral metal-organic porous material
- CSP:
-
Chiral stationary phase
- dca:
-
dicyanamide
- DPEN:
-
1,2-diphenylethylenediamine
- IRMOF:
-
Isoreticular metal organic framework
- lac:
-
Lactate
- MOF:
-
Metal-organic framework
- MOPM:
-
Metal-organic porous material
- pic:
-
picoline
- QA:
-
6-methoxyl-(8S,9R)-cinchonan-9-ol-3-carboxylate
- sala:
-
N-(2-hydroxybenzyl)-l-alanine
- salen:
-
1,2-cyclohexanediimino-salicylidene
- SBU:
-
Secondary building unit
- SHG:
-
Second harmonic generation
- TOF:
-
Turn over frequency
- TON:
-
Turn over number
- UHP:
-
Urea hydroperoxide
References
Corma A (1997) Chem Rev 97:2373
Maesen TLM, Marcus B (2001) In: van Bekkum H, Flanigen EM, Jacobs PA, Jansen JC (eds) Introduction to zeolite science and practice. Elsevier, Amsterdam, p 1
Song CE, Lee SG (2002) Chem Rev 102:3495
Newsam JM, Treacy MMJ, Koetsier WT, de Gruyter CB (1988) Proc R Soc Lond Ser A 420:375
Anderson MW, Terasaki O, Ohsuna T, Philippou A, MacKay SP, Ferreira A, Rocha J, Lidin S (1994) Nature 367:347
Janiak C (2003) Dalton Trans:2781
James SL (2003) Chem Soc Rev 32:276
Rosseinsky MJ (2004) Microporus Mesoporous Mater 73:15
Rowsell JLC, Yaghi OM (2005) Angew Chem Int Ed 44:4670
Férey G (2008) Chem Soc Rev 37:191
Morris RE, Wheatley PS (2008) Angew Chem Int Ed 47:4966
Lin W (2005) J Solid State Chem 178:2486
Lin W (2005) Top Catal 34:85
Lin W (2007) MRS Bull 32:544
Wells AF (1977) Three-dimensional nets and polyhedra. Wiley, New York
Janiak C (1997) Angew Chem Int Ed Engl 36:1431
Kondo M, Okubo T, Asami A, Noro SI, Yoshitomi T, Kitagawa S, Ishii T, Matsuzaka H, Seki K (1999) Angew Chem Int Ed 38:140
Moulton B, Zaworotko MJ (2001) Chem Rev 101:1629 and references therein
Khlobystov AN, Blake AJ, Champness NR, Lemenovskii DA, Majouga AG, Zyk NV, Schröder M (2001) Coord Chem Rev 222:155
Barnett SA, Champness NR (2003) Coord Chem Rev 246:145
Desiraju GR (1989) Crystal engineering. The design of organic solids. Elsevier, Amsterdam
Desiraju GR (2002) Acc Chem Res 35:565 and references therein
Steiner T (2002) Angew Chem Int Ed 41:48
Hoskins BF, Robson R (1990) J Am Chem Soc 112:1546
Biradha K, Seward C, Zaworotko MJ (1999) Angew Chem Int Ed 38:492
Zaworotko MJ (2000) Angew Chem Int Ed 39:3052
Yaghi OM, Li H, Davis C, Richardson D, Groy TL (1998) Acc Chem Res 31:474
Eddaoudi M, Moler DB, Li H, Chen B, Reineke TM, O’Keeffe M, Yaghi OM (2001) Acc Chem Res 34:319
Wang Z, Kravtsov VC, Zaworotko MJ (2005) Angew Chem Int Ed 44:2877
Eddaoudi M, Kim J, Rosi N, Vodak D, O’Keeffe M, Yaghi OM (2002) Science 295:469
Yaghi OM, O’Keeffe M, Ockwig N, Chae HK, Eddaoudi M, Kim J (2003) Nature 423:705
Ockwig N, Friedrichs OD, O’Keeffe M, Yaghi OM (2005) Acc Chem Res 38:176
Zhang JP, Lin YY, Huang XC, Chen XM (2005) J Am Chem Soc 127:5495
Evans OR, Lin W (2002) Acc Chem Res 35:511
Halder GJ, Kepert CJ, Moubaraki B, Murray KS, Cashion JD (2002) Science 298:1762
Dincă M, Long JR (2007) J Am Chem Soc 129:11172
Noro S, Kitagawa S, Kondo M, Seki K (2000) Angew Chem Int Ed 39:2081
Rosi NL, Eckert J, Eddaoidi M, Vodak DT, Kim J, O’Keeffe M, Yaghi OM (2003) Science 300:1127
Kitagawa S, Kitaura R, Noro S (2004) Angew Chem Int Ed 43:2334
Fujita M, Kwon YJ, Washizu S, Ogura K (1994) J Am Chem Soc 116:1151
Seo JS, Whang D, Lee H, Jun SI, Oh J, Jeon Y, Kim K (2000) Nature 404:982
Joy A, Ramamurthy V (2000) Chem Eur J 6:1287
Sivasubramanian K, Kaanumalle LS, Uppili S, Ramamurthy V (2007) Org Biomol Chem 5:1569
Withersby MA, Blake AJ, Champness NR, Hubberstey P, Li WS, Schröder M (1997) Angew Chem Int Ed Engl 36:2327
Batten SR, Hoskins BF, Robson R (1997) Angew Chem Int Ed Engl 36:636
Krämer R, Lehn JM, De Cian A, Fischer J (1993) Angew Chem Int Ed Engl 32:703
Chen XD, Du M, Mak TCW (2005) Chem Commun:4417
Abrahams BF, Jackson PA, Robson R (1998) Angew Chem Int Ed 37:2656
Kepert CJ, Rosseinsky MJ (1998) Chem Commun:31
Kepert CJ, Prior TJ, Rosseinsky MJ (2000) J Am Chem Soc 122:5158
Lin Z, Slawin AMZ, Morris RE (2007) J Am Chem Soc 129:4880
Ranford JD, Vittal JJ, Wu D (1998) Angew Chem Int Ed 37:1114
Kesanli B, Cui Y, Smith MR, Bittner EW, Bockrath BC, Lin W (2005) Angew Chem Int Ed 44:72
Cho SH, Ma B, Nguyen ST, Hupp JT, Albrecht-Schmitt TE (2006) Chem Commun:2563
Zhang J, Liu R, Feng P, Bu X (2007) Angew Chem Int Ed 46:8388
Dybtsev DN, Nuzhdin AL, Chun H, Bryliakov KP, Talsi EP, Fedin VP, Kim K (2006) Angew Chem Int Ed 45:916
Vaidhyanathan R, Bradshaw D, Rebilly JN, Barrio JP, Gould JA, Berry NG, Rosseinsky MJ (2006) Angew Chem Int Ed 45:6495
Hasegawa S, Horike S, Matsuda R, Furukawa S, Mochizuki K, Kinoshita Y, Kitagawa S (2007) J Am Chem Soc 129:2607
Wang Z, Cohen SM (2007) J Am Chem Soc 129:12368
Tanabe KK, Wang Z, Cohen SM (2008) J Am Chem Soc 130:8508
Hwang YK, Hong DY, Chang JS, Jhung SH, Seo YK, Kim J, Vimont A, Daturi M, Serre C, Férey G (2008) Angew Chem Int Ed 47:4144
Collins AN, Sheldrake GN, Crosby J (1996) Chirality in industry. Wiley, NY
Blaser HU, Spindler F, Studer M (2001) Appl Catal A Gen 221:119
Oehme G (1999) In: Jacobsen EN, Pfaltz A, Yamamoto H (eds) Comprehensive Asymmetric Catalysis. Springer-Verlag, Berlin, Vol 3, p 1378
Heitbaum M, Glorius F, Escher I (2006) Angew Chem Int Ed 45:4732
McMorn P, Hutchings GJ (2004) Chem Soc Rev 33:108
Sherrington DC (2000) Catal Today 57:87
Ding K, Wang Z, Wang X, Liang Y, Wang X (2006) Chem Eur J 12:5188
Pini D, Mandoli A, Orlandi S, Salvadori P (1999) Tetrahedron Asymmetry 10:3883
Ward TJ (2006) Anal Chem 78:3947
Maier NM, Lindner W (2007) Anal Bioanal Chem 389:377
Gübitz G, Martin G, Schmid MG (2007) Electrophoresis 28:114
Cancelliere G, D’Acquarica I, Gasparrini F, Maggini M, Misiti D, Villani C (2006) J Sep Sci 29:770
Xiong RG, You XZ, Abrahams BF, Xue ZL, Che CM (2001) Angew Chem Int Ed 40:4422
Xie YR, Wang XS, Zhao H, Zhang J, Weng LH, Duan CY, Xiong RG, You XZ, Xue ZL (2003) Organometallics 22:4396
Song YM, Zhou T, Wang XS, Li XN, Xiong RG (2006) Cryst Growth Des 6:14
Bradshaw D, Prior TJ, Cussen EJ, Claridge JB, Rosseinsky MJ (2004) J Am Chem Soc 126:6106
Nuzhdin AL, Dybtsev DN, Bryliakov KP, Talsi EP, Fedin VP (2007) J Am Chem Soc 129:12958
Muppidi VK, Zacharias PS, Pal S (2005) Chem Commun:2515
Muppidi VK, Zacharias PS, Pal S (2007) J Solid State Chem 180:132
Sawaki T, Dewa T, Aoyama Y (1998) J Am Chem Soc 120:8539
Gao Y, Wada T, Yang K, Kim K, Inoue Y (2005) Chirality 17:S19
Evans OR, Ngo HL, Lin W (2001) J Am Chem Soc 123:10395
Hu A, Ngo HL, Lin W (2003) Angew Chem Int Ed 42:6000
Hu A, Ngo HL, Lin W (2003) J Am Chem Soc 125:11490
Ngo HL, Hu A, Lin W (2004) J Mol Catal A Chem 215:177
Wu CD, Hu A, Zhang L, Lin W (2005) J Am Chem Soc 127:8940
Wu CD, Lin W (2007) Angew Chem Int Ed 46:1075
Ohkuma T, Ooka H, Ikariya T, Noyori R (1995) J Am Chem Soc 117:10417
Doucet H, Ohkuma T, Murata K, Yokozawa T, Kozawa M, Katayama E, England AF, Ikariya T, Noyori R (1998) Angew Chem Int Ed 37:1703
Jiang H, Lin W (2004) Org Lett 6:861
Tanaka K, Oda S, Shiro M (2008) Chem Commun:820
Ingleson MJ, Barrio JP, Bacsa J, Dickinson C, Park H, Rosseinsky MJ (2008) Chem Commun:1287
Gu ZG, Zhou XH, Jin YB, Xiong RG, Zuo JL, You XZ (2007) Inorg Chem 46:5462
Zang S, Su Y, Li Y, Ni Z, Meng Q (2006) Inorg Chem 45:174
Xie YR, Zhao H, Wang XS, Qu ZR, Xiong RG, Xue X, Xue Z, You XZ (2003) Eur J Inorg Chem 3712
Zang S, Su Y, Li Y, Zhu H, Meng Q (2006) Inorg Chem 45:2972
Sun D, Ke Y, Collins DJ, Lorigan GA, Zhou HC (2007) Inorg Chem 46:2725
Lee HN, Christen HM, Chisholm MF, Rouleau CM, Lowndes DH (2005) Nature 433:395
Gao EQ, Yue YF, Bai SQ, He Z, Yan CH (2004) J Am Chem Soc 126:1419
Inoue K, Kikuchi K, Ohba M, Okawa H (2003) Angew Chem Int Ed 42:4810
Imai H, Inoue K, Kikuchi K, Yoshida Y, Ito M, Sunahara T, Onaka S (2004) Angew Chem Int Ed 43:5618
Wen HR, Wang CF, Song Y, Zuo JL, You XZ (2005) Inorg Chem 44:9039
Liu WL, Song Y, Li YZ, Zou Y, Dang DB, Ni CL, Meng QJ (2004) Chem Commun:2348
Wang L, Yang M, Li G, Shi Z, Feng S (2006) Inorg Chem 45:2474
Yue Q, Yang J, Li GH, Li GD, Chen JS (2006) Inorg Chem 45:4431
Roques N, Mugnaini V, Veciana J (2009) Magnetic and porous molecule-based materials. Top Curr Chem. doi:10.1007/128_2009_8
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2009 Springer
About this chapter
Cite this chapter
Kim, K., Banerjee, M., Yoon, M., Das, S. (2009). Chiral Metal-Organic Porous Materials: Synthetic Strategies and Applications in Chiral Separation and Catalysis. In: Schröder, M. (eds) Functional Metal-Organic Frameworks: Gas Storage, Separation and Catalysis. Topics in Current Chemistry, vol 293. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2009_7
Download citation
DOI: https://doi.org/10.1007/128_2009_7
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-14612-1
Online ISBN: 978-3-642-14613-8
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)