RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2017; 49(18): 4341-4349
DOI: 10.1055/s-0036-1590803
DOI: 10.1055/s-0036-1590803
paper
An Efficient Cascade Synthesis of Ethyl 3-Amino-5-oxoisoxazolidine-4-carboxylate Derivatives
We are grateful for financial support from the National Natural Science Foundation of China (No. 81673287).Weitere Informationen
Publikationsverlauf
Received: 01. April 2017
Accepted after revision: 25. Mai 2017
Publikationsdatum:
11. Juli 2017 (online)
Abstract
An efficient cascade synthesis of ethyl 3-amino-5-oxoisoxazolidine-4-carboxylate derivatives from diethyl 2-(ethoxymethylene)malonate, different hydroxylamines and various amines is developed. This approach tolerates a wide range of amines affording highly functionalized isoxazolidine derivatives, which are expected to be important in organic synthesis and medicinal chemistry.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1590803.
- Supporting Information
-
References
- 1a Overy D. Calati K. Nielsen-Kahn J. Hsu M.-J. Martin J. Collado J. Roemer T. Harris G. Parish CA. Bioorg. Med. Chem. 2009; 19: 1224
- 1b Janecki T. Wasek T. Rozalski M. Krajewska U. Studzian K. Janecka A. Bioorg. Med. Chem. 2006; 16: 1430
- 1c Cao X. Iqbal A. Patel A. Gretz P. Huang G. Crowder M. Day RA. Biochem. Biophys. Res. Commun. 2003; 311: 267
- 1d Li YX. Kinami K. Hirokami Y. Kato A. Su JK. Jia YM. Fleet GW. Yu CY. Org. Biomol. Chem. 2016; 14: 2249
- 2a Baldwin JE. Adlington RM. Mellor LC. Tetrahedron 1994; 50: 5049
- 2b Baldwin JE. Adlington RM. Birch DJ. J. Chem. Soc., Chem. Commun. 1985; 256
- 2c Tite T. Sabbah M. Levacher V. Briere J.-F. Chem. Commun. 2013; 49: 11569
- 2d Moglioni AG. Muray E. Castillo JA. Larena Á. Á. Moltrasio GY. Branchadell V. Ortuño RM. J. Org. Chem. 2002; 67: 2402
- 2e Hafren JF. Cordova A. WO2008020007A2, 2008
- 2f Bentley SA. Davies SG. Lee JA. Roberts PM. Russell AJ. Thomson JE. Toms SM. Tetrahedron 2010; 66: 4604
- 2g Shindo M. Itoh K. Ohtsuki K. Tsuchiya C. Shishido K. Synthesis 2003; 1441
- 3 Romeo G. Chiacchio U. Corsaro A. Merino P. Chem. Rev. 2010; 110: 3337
- 4 Socha D. Jurczak M. Chmielewski M. Tetrahedron 1991; 53: 739
- 5 Juarez-Garcia ME. Yu S. Bode JW. Tetrahedron 2010; 66: 4841
- 6a Surya Prakash GK. Zhang Z. Wang F. Rahm M. Ni C. Iuliucci M. Haiges R. Olah GA. Chem. Eur. J. 2014; 20: 831
- 6b Shindo M. Ohtsuki K. Shishido K. Tetrahedron: Asymmetry 2005; 16: 2821
- 6c Luisi R. Capriati V. Florio S. Vista T. J. Org. Chem. 2003; 68: 9861
- 6d Shindo KI. M. Tsuchiya C. Shishido K. Org. Lett. 2002; 4: 3119
- 6e Luisi R. Capriati V. Degennaro L. Florio S. Org. Lett. 2003; 5: 2723
- 7a Sibi MP. Liu M. Org. Lett. 2001; 3: 4181
- 7b Sibi MP. Liu M. Org. Lett. 2000; 2: 3393
- 7c Lee H.-S. Park J.-S. Kim BM. Gellman SH. J. Org. Chem. 2003; 68: 1575
- 7d Izumi S. Kobayashi Y. Takemoto Y. Org. Lett. 2016; 18: 696
- 7e Tabarki MA. Besbes R. Tetrahedron 2014; 70: 1060
- 7f Keen SP. Weinreb SM. Tetrahedron Lett. 2000; 41: 4307
- 7g Cardillo G. Gentilucci L. Gianotti M. Perciaccante R. Tolomelli A. J. Org. Chem. 2001; 66: 8657
- 8a Brauch S. van Berkel SS. Westermann B. Chem. Soc. Rev. 2013; 42: 4948
- 8b Shiri M. Chem. Rev. 2012; 112: 3508
- 8c Ganem B. Acc. Chem. Res. 2009; 42: 463
- 8d Toure BB. Hal DG. Chem. Rev. 2009; 109: 4439
- 9 Berini C. Sebban M. Oulyadi H. Sanselme M. Levacher V. Briere JF. Org. Lett. 2015; 17: 5408
- 10 Coilis MP. Hockless DC. R. Perlmutter P. Tetrahedron Lett. 1995; 36: 7133
- 11a Wang J. Qi C. Ge Z. Cheng T. Li R. Chem. Commun. 2010; 46: 2124
- 11b Wang W. Wang J. Zhou S. Sun Q. Ge Z. Wang X. Li R. Chem. Commun. 2013; 49: 1333
- 11c Bai Z. Ji L. Ge Z. Wang X. Li R. Org. Biomol. Chem. 2015; 13: 5363
- 12 Beccalli EM. Rosa CL. Marchesini A. J. Org. Chem. 1984; 49: 4287
- 13 Nishiwaki N. Kobiro K. Kiyoto H. Hirao S. Sawayama J. Saigo K. Okajima Y. Uehara T. Maki A. Ariga M. Org. Biomol. Chem. 2011; 9: 2832