Synthesis of 2-aryl-3-(2-cyanoethyl)aziridines and their chemical and enzymatic hydrolysis towards γ-lactams and γ-lactones

作者: Karen Mollet , Lena Decuyper , Saskia Vander Meeren , Nicola Piens , Karel De Winter

DOI: 10.1039/C4OB02615B

关键词: Organic synthesisEnzymatic hydrolysisNitrilaseHydrolysisBiocatalysisNitrileOrganic chemistryArylChemistryAlkylation

摘要: Trans- andcis-2-aryl-3-(2-cyanoethyl)aziridines were transformed into 4-[aryl(alkylamino)methyl]butyrolactones and/or 5-[aryl(hydroxy)methyl]pyrrolidin-2-onesviachemical and enzymatic hydrolysis of the cyano group, followed by ring expansion.

参考文章(50)
G. C. Volgas, Bala N. Devisetty, R. Scott Tann, Franklin R. Hall, Tann R. Scott, Roger A. Downer, H. B. Lopez, Paul D. Berger, Alan K. Viets, David A. Hovde, David G. Chasin, Herbert M. Collins, Michael J. Hopkinson, John D. Nalewaja, Loren E. Bode, Jane C. Mueninghoff, James L. Hazen, G. Robert Goss, G. B. Beestman, Pesticide Formulations and Application Systems ,(1987)
Saron Catak, Matthias D’hooghe, Toon Verstraelen, Karen Hemelsoet, Andries Van Nieuwenhove, Hyun-Joon Ha, Michel Waroquier, Norbert De Kimpe, Veronique Van Speybroeck, Opposite regiospecific ring opening of 2-(cyanomethyl)aziridines by hydrogen bromide and benzyl bromide: experimental study and theoretical rationalization. Journal of Organic Chemistry. ,vol. 75, pp. 4530- 4541 ,(2010) , 10.1021/JO100687Q
Benito Alcaide, Pedro Almendros, Cristina Aragoncillo, β-Lactams: Versatile Building Blocks for the Stereoselective Synthesis of Non-β-Lactam Products Chemical Reviews. ,vol. 107, pp. 4437- 4492 ,(2007) , 10.1021/CR0307300
Stuart M Thomas, Robert DiCosimo, Vasantha Nagarajan, Biocatalysis: applications and potentials for the chemical industry. Trends in Biotechnology. ,vol. 20, pp. 238- 242 ,(2002) , 10.1016/S0167-7799(02)01935-2
Iwao Ojima, Recent Advances in the .beta.-Lactam Synthon Method Accounts of Chemical Research. ,vol. 28, pp. 383- 389 ,(1995) , 10.1021/AR00057A004
Jed F. Fisher, Samy O. Meroueh, Shahriar Mobashery, Bacterial Resistance to β-Lactam Antibiotics: Compelling Opportunism, Compelling Opportunity† Chemical Reviews. ,vol. 105, pp. 395- 424 ,(2005) , 10.1021/CR030102I
Margit Winkler, Ludmila Martínková, Astrid C. Knall, Stefan Krahulec, Norbert Klempier, Synthesis and microbial transformation of β-amino nitriles Tetrahedron. ,vol. 61, pp. 4249- 4260 ,(2005) , 10.1016/J.TET.2005.02.057
Duncan J. Wardrop, Edward G. Bowen, Raymond E. Forslund, Adam D. Sussman, Samanthi L. Weerasekera, Intramolecular oxamidation of unsaturated O-alkyl hydroxamates: a remarkably versatile entry to hydroxy lactams. Journal of the American Chemical Society. ,vol. 132, pp. 1188- 1189 ,(2010) , 10.1021/JA9069997
Michihiko Kobayashi, Toru Nagasawa, Hideaki Yamada, Enzymatic synthesis of acrylamide: a success story not yet over. Trends in Biotechnology. ,vol. 10, pp. 402- 408 ,(1992) , 10.1016/0167-7799(92)90283-2
Berten Van Driessche, Willem Van Brabandt, Matthias D'hooghe, Yves Dejaegher, Norbert De Kimpe, Synthesis and reactivity of trans-2-aryl-3-chloroazetidines Tetrahedron. ,vol. 62, pp. 6882- 6892 ,(2006) , 10.1016/J.TET.2006.04.104