16. Larsson ALE, Persson BA, Bäckvall JE (1997) Enzymatic resolution of alcohols coupled with
ruthenium-catalyzed racemization of the substrate alcohol. Angew Chem Int Ed 36:211–1212
17. Dinh PM, Howarth JA, Hudnott AR, Williams JMJ, Harris W (1996) Catalytic racemization
of alcohols: applications to enzymatic resolution reactions. Tetrahedron Lett 37:7623–7626.
https://doi.org/10.1016/0040-4039(96)01677-2
18. Allen JV, Williams JMJ (1996) Dynamic kinetic resolution with enzyme and palladium
combinations. Tetrahedron Lett 37:1859–1862. https://doi.org/10.1016/0040-4039(96)
00136-0
19. Martín-Matute B, Edin M, Bogár K, Bäckvall JE (2004) Highly compatible metal and enzyme
catalysts for efficient dynamic kinetic resolution of alcohols at ambient temperature. Angew
Chem Int Ed 43:6535–6539. https://doi.org/10.1002/anie.200461416
20. Fernández-Salas JA, Manzini S, Nolan SP (2014) A cationic ruthenium complex for the
dynamic kinetic resolution of secondary alcohols. Chem Eur J 20:13132–13135. https://doi.
org/10.1002/chem.201404096
21. Mavrynsky D, Päiviö M, Lundell K, Sillanpää R, Kanerva LT, Leino R (2009)
Dicarbonylchloro(pentabenzylcyclopentadienyl)ruthenium as racemization catalyst in the
dynamic kinetic resolution of secondary alcohols. Eur J Org Chem 2009:1317–1320. https://
doi.org/10.1002/ejoc.200801248
22. Kim MJ, Chung YI, Choi YK, Lee HK, Kim D, Park J (2003) (S)-selective
dynamic kinetic resolution of secondary alcohols by the combination of subtilisin
and an aminocyclopentadienylruthenium complex as the catalysts. J Am Chem Soc
125:11494–11495. https://doi.org/10.1021/ja036766r
23. Parvulescu A, Janssens J, Vanderleyden J, De Vos D (2010) Heterogeneous catalysts
for racemization and dynamic kinetic resolution of amines and secondary alcohols. Top
Catal 53:931–941. https://doi.org/10.1007/s11244-010-9512-x
24. Reetz MT, Schimossek K (1996) Lipase-catalyzed dynamic kinetic resolution of chiral
amines. Use of palladium as the racemization catalyst. Chimia 50:668–669
25. Parvulescu AN, Jacobs PA, De Vos DE (2007) Palladium catalysts on alkaline-earth supports
for racemization and dynamic kinetic resolution of benzylic amines. Chem Eur J
13:2034–2043. https://doi.org/10.1002/chem.200600899
26. Parvulescu A, De Vos D, Jacobs P (2005) Efficient dynamic kinetic resolution of secondary
amines with Pd on alkaline earth salts and a lipase. Chem Commun (42):5307–5309. https://
doi.org/10.1039/B509747A
27. Engström K, Shakeri M, Bäckvall JE (2011) Dynamic kinetic resolution of β-amino esters
by a heterogeneous system of a palladium nanocatalyst and Candida antarctica lipase A. Eur J
Org Chem 2011:1827–1830. https://doi.org/10.1002/ejoc.201001714
28. Choi YK, Kim Y, Han K, Park J, Kim MJ (2009) Synthesis of optically active amino acid
derivatives via dynamic kinetic resolution. J Org Chem 74:9543–9545. https://doi.org/10.
1021/jo902034x
29. Kim MJ, Kim WH, Han K, Choi YK, Park J (2007) Dynamic kinetic resolution of primary
amines with a recyclable Pd nanocatalyst for racemization. Org Lett 9:1157–1159. https://doi.
org/10.1021/ol070130d
30. Xu G, Dai X, Fu S, Wu J, Yang L (2014) Efficient dynamic kinetic resolution of arylamines
with Pd/layered double-hydroxide-dodecyl sulfate anion for racemization. Tetrahedron Lett
55:397–402. https://doi.org/10.1016/j.tetlet.2013.11.041
31. Xu Y, Wang M, Feng B, Li Z, Li Y, Li H, Li H (2017) Dynamic kinetic resolution of aromatic
sec-alcohols by using a heterogeneous palladium racemization catalyst and lipase. Cat Sci
Technol 7:5838–5842. https://doi.org/10.1039/C7CY01954H
32. Jin Q, Jia G, Zhang Y, Li C (2014) Modification of supported Pd catalysts by alkalic salts
in the selective racemization and dynamic kinetic resolution of primary amines. Cat Sci
Technol 4:464–471. https://doi.org/10.1039/C3CY00535F
33. Gustafson KPJ, Lihammar R, Verho O, Engström K, Bäckvall JE (2014) Chemoenzymatic
dynamic kinetic resolution of primary amines using a recyclable palladium nanoparticle
catalyst together with lipases. J Org Chem 79:3747–3751. https://doi.org/10.1021/jo500508p
Nanocatalysis Meets Biology
271
ruthenium-catalyzed racemization of the substrate alcohol. Angew Chem Int Ed 36:211–1212
17. Dinh PM, Howarth JA, Hudnott AR, Williams JMJ, Harris W (1996) Catalytic racemization
of alcohols: applications to enzymatic resolution reactions. Tetrahedron Lett 37:7623–7626.
https://doi.org/10.1016/0040-4039(96)01677-2
18. Allen JV, Williams JMJ (1996) Dynamic kinetic resolution with enzyme and palladium
combinations. Tetrahedron Lett 37:1859–1862. https://doi.org/10.1016/0040-4039(96)
00136-0
19. Martín-Matute B, Edin M, Bogár K, Bäckvall JE (2004) Highly compatible metal and enzyme
catalysts for efficient dynamic kinetic resolution of alcohols at ambient temperature. Angew
Chem Int Ed 43:6535–6539. https://doi.org/10.1002/anie.200461416
20. Fernández-Salas JA, Manzini S, Nolan SP (2014) A cationic ruthenium complex for the
dynamic kinetic resolution of secondary alcohols. Chem Eur J 20:13132–13135. https://doi.
org/10.1002/chem.201404096
21. Mavrynsky D, Päiviö M, Lundell K, Sillanpää R, Kanerva LT, Leino R (2009)
Dicarbonylchloro(pentabenzylcyclopentadienyl)ruthenium as racemization catalyst in the
dynamic kinetic resolution of secondary alcohols. Eur J Org Chem 2009:1317–1320. https://
doi.org/10.1002/ejoc.200801248
22. Kim MJ, Chung YI, Choi YK, Lee HK, Kim D, Park J (2003) (S)-selective
dynamic kinetic resolution of secondary alcohols by the combination of subtilisin
and an aminocyclopentadienylruthenium complex as the catalysts. J Am Chem Soc
125:11494–11495. https://doi.org/10.1021/ja036766r
23. Parvulescu A, Janssens J, Vanderleyden J, De Vos D (2010) Heterogeneous catalysts
for racemization and dynamic kinetic resolution of amines and secondary alcohols. Top
Catal 53:931–941. https://doi.org/10.1007/s11244-010-9512-x
24. Reetz MT, Schimossek K (1996) Lipase-catalyzed dynamic kinetic resolution of chiral
amines. Use of palladium as the racemization catalyst. Chimia 50:668–669
25. Parvulescu AN, Jacobs PA, De Vos DE (2007) Palladium catalysts on alkaline-earth supports
for racemization and dynamic kinetic resolution of benzylic amines. Chem Eur J
13:2034–2043. https://doi.org/10.1002/chem.200600899
26. Parvulescu A, De Vos D, Jacobs P (2005) Efficient dynamic kinetic resolution of secondary
amines with Pd on alkaline earth salts and a lipase. Chem Commun (42):5307–5309. https://
doi.org/10.1039/B509747A
27. Engström K, Shakeri M, Bäckvall JE (2011) Dynamic kinetic resolution of β-amino esters
by a heterogeneous system of a palladium nanocatalyst and Candida antarctica lipase A. Eur J
Org Chem 2011:1827–1830. https://doi.org/10.1002/ejoc.201001714
28. Choi YK, Kim Y, Han K, Park J, Kim MJ (2009) Synthesis of optically active amino acid
derivatives via dynamic kinetic resolution. J Org Chem 74:9543–9545. https://doi.org/10.
1021/jo902034x
29. Kim MJ, Kim WH, Han K, Choi YK, Park J (2007) Dynamic kinetic resolution of primary
amines with a recyclable Pd nanocatalyst for racemization. Org Lett 9:1157–1159. https://doi.
org/10.1021/ol070130d
30. Xu G, Dai X, Fu S, Wu J, Yang L (2014) Efficient dynamic kinetic resolution of arylamines
with Pd/layered double-hydroxide-dodecyl sulfate anion for racemization. Tetrahedron Lett
55:397–402. https://doi.org/10.1016/j.tetlet.2013.11.041
31. Xu Y, Wang M, Feng B, Li Z, Li Y, Li H, Li H (2017) Dynamic kinetic resolution of aromatic
sec-alcohols by using a heterogeneous palladium racemization catalyst and lipase. Cat Sci
Technol 7:5838–5842. https://doi.org/10.1039/C7CY01954H
32. Jin Q, Jia G, Zhang Y, Li C (2014) Modification of supported Pd catalysts by alkalic salts
in the selective racemization and dynamic kinetic resolution of primary amines. Cat Sci
Technol 4:464–471. https://doi.org/10.1039/C3CY00535F
33. Gustafson KPJ, Lihammar R, Verho O, Engström K, Bäckvall JE (2014) Chemoenzymatic
dynamic kinetic resolution of primary amines using a recyclable palladium nanoparticle
catalyst together with lipases. J Org Chem 79:3747–3751. https://doi.org/10.1021/jo500508p
Nanocatalysis Meets Biology
271