Directed (R)- or (S)-Selective Dynamic Kinetic Enzymatic Hydrolysis of 1,2,3,4-Tetrahydroisoquinoline-1-carboxylic Esters

作者: Tihamér A Paál , Arto Liljeblad , Liisa T Kanerva , Enikő Forró , Ferenc Fülöp

DOI: 10.1002/EJOC.200800789

关键词:

摘要: The first synthesis of both enantiomers 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid was accomplished through dynamic kinetic resolution in procedures based on CAL-B- or subtilisin Carlsberg-catalysed enantioselective hydrolysis the corresponding ethyl esters aqueous NH4OAc buffer at pH 8.5. products were obtained with high enantiopurity (92–93 % ee) good yields (85–92 %). (R)-1,2,3,4-Tetrahydroisoquinoline-1-carboxylic (98 % ee) and yield (85 %) a CAL-B-catalysed process, under similar conditions.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

参考文章(29)
Béla E Tóth, Ibolya Bodnár, Krisztián G Homicskó, Ferenc Fülöp, Márton IK Fekete, György M Nagy, None, Physiological role of salsolinol: its hypophysiotrophic function in the regulation of pituitary prolactin secretion. Neurotoxicology and Teratology. ,vol. 24, pp. 655- 666 ,(2002) , 10.1016/S0892-0362(02)00216-7
Natalie J Carter, Lesley J Scott, Human Plasma von Willebrand Factor/Factor VIII Complex (Haemate® P/Humate-P®) Drugs. ,vol. 67, pp. 1513- 1519 ,(2012) , 10.2165/00003495-200767100-00009
Dario Arosio, Antonio Caligiuri, Paola D'Arrigo, Giuseppe Pedrocchi-Fantoni, Cristina Rossi, Caterina Saraceno, Stefano Servi, Davide Tessaro, Chemo-Enzymatic Dynamic Kinetic Resolution of Amino Acid Thioesters Advanced Synthesis & Catalysis. ,vol. 349, pp. 1345- 1348 ,(2007) , 10.1002/ADSC.200700050
Ole Kirk, Morten Würtz Christensen, Lipases from Candida antarctica: Unique Biocatalysts from a Unique Origin Organic Process Research & Development. ,vol. 6, pp. 446- 451 ,(2002) , 10.1021/OP0200165
Tihamér A Paál, Enikő Forró, Arto Liljeblad, Liisa T Kanerva, Ferenc Fülöp, None, Lipase-catalyzed kinetic and dynamic kinetic resolution of 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid Tetrahedron-asymmetry. ,vol. 18, pp. 1428- 1433 ,(2007) , 10.1016/J.TETASY.2007.05.016
Jack D. Scott, Robert M. Williams, Chemistry and biology of the tetrahydroisoquinoline antitumor antibiotics. Chemical Reviews. ,vol. 102, pp. 1669- 1730 ,(2002) , 10.1021/CR010212U
Zita Zalán, Tamás A Martinek, László Lázár, Reijo Sillanpää, Ferenc Fülöp, None, Synthesis and conformational analysis of tetrahydroisoquinoline- and piperidine-fused 1,3,4,2-oxadiazaphosphinanes, new ring systems Tetrahedron. ,vol. 62, pp. 2883- 2891 ,(2006) , 10.1016/J.TET.2006.01.018
Iqbal S. Gill, Ellen Kick, Kate Richlin-Zack, Wu Yang, Yufeng Wang, Ramesh N. Patel, Enzymatic resolution of methyl (1RS)-N-tBoc-6-hydroxy-3,4-dihydro-1H-isoquinoline-1-carboxylate by Seaprose S Tetrahedron-asymmetry. ,vol. 18, pp. 2147- 2154 ,(2007) , 10.1016/J.TETASY.2007.09.011
B. Anders Persson, Anna L. E. Larsson, Mikaël Le Ray, Jan-E. Bäckvall, Ruthenium- and enzyme-catalyzed dynamic kinetic resolution of secondary alcohols Journal of the American Chemical Society. ,vol. 121, pp. 1645- 1650 ,(1999) , 10.1021/JA983819+