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Synthesis 2018; 50(02): 323-329
DOI: 10.1055/s-0036-1590928
DOI: 10.1055/s-0036-1590928
paper
Organocatalytic Enantioselective Vinylogous Henry Reaction of 3,5-Dimethyl-4-nitroisoxazole with Trifluoromethyl Ketones
Authors
Weitere Informationen
Publikationsverlauf
Received: 05. September 2017
Accepted: 12. September 2017
Publikationsdatum:
04. Oktober 2017 (online)
Abstract
The enantioselective vinylogous Henry reaction of 3,5-dimethyl-4-nitroisoxazole with trifluoromethyl ketones employing a bifunctional squaramide organocatalyst has been developed. A series of isoxazole bearing trifluoromethyl-substituted tertiary alcohols, 2-substituted (R)-1,1,1-trifluoro-3-(3-methyl-4-nitroisoxazol-5-yl)propan-2-ols, were obtained under these mild reaction conditions in good yields and moderate to good enantioselectivities
Key words
asymmetric synthesis - isoxazole - trifluoromethyl ketone - squaramide organocatalyst - vinylogous Henry reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1590928.
- Supporting Information (PDF)
-
References
- 1a Boldon S. Moore JE. Gouverneur V. Chem. Commun. 2008; 3622
- 1b Kim DW. Jeong H.-J. Lim ST. Sohn M.-H. Angew. Chem. Int. Ed. 2008; 47: 8404
- 1c Bondalapati S. Reddy UC. Kundu DS. Saikia AK. J. Fluorine Chem. 2010; 131: 320
- 1d Furuya T. Kamlet AS. Ritter T. Nature (London) 2011; 473: 470
- 1e Bizet V. Besset T. Ma JA. Cahard D. Curr. Top. Med. Chem. 2014; 14: 901
- 1f Champagne PA. Desroches J. Hamel J.-D. Vandamme M. Paquin J.-F. Chem. Rev. 2015; 115: 9073
- 2 Jeschke P. ChemBioChem 2004; 5: 570
- 3a Kirk KL. J. Fluorine Chem. 2006; 127: 1013
- 3b Purser S. Moore PR. Swallow S. Gouverneur V. Chem. Soc. Rev. 2008; 37: 320
- 4 Tirotta I. Dichiarante V. Pigliacelli C. Cavallo G. Terraneo G. Baldelli Bombelli F. Metrangolo P. Resnati G. Chem. Rev. 2015; 115: 1106
- 5a Pagliaro M. Ciriminna R. J. Mater. Chem. 2005; 15: 4981
- 5b Berger R. Resnati G. Metrangolo P. Weber E. Hulliger J. Chem. Soc. Rev. 2011; 40: 3496
- 6 Wang J. Sánchez-Roselló M. Aceña JL. del Pozo C. Sorochinsky AE. Fustero S. Soloshonok VA. Liu H. Chem. Rev. 2014; 114: 2432
- 7 Kelly CB. Mercadante MA. Leadbeater NE. Chem. Commun. 2013; 49: 11133
- 8a Martina SL. X. Jagt RB. C. de Vries JG. Feringa BL. Minnaard AJ. Chem. Commun. 2006; 4093
- 8b Motoki R. Tomita D. Kanai M. Shibasaki M. Tetrahedron Lett. 2006; 47: 8083
- 8c Tur F. Saá JM. Org. Lett. 2007; 9: 5079
- 8d Yearick K. Wolf C. Org. Lett. 2008; 10: 3915
- 8e Blay G. Fernández I. Monleón A. Pedro JR. Vila C. Org. Lett. 2009; 11: 441
- 8f Xu H. Wolf C. Chem. Commun. 2010; 46: 8026
- 8g Zhang G.-W. Meng W. Ma H. Nie J. Zhang W.-Q. Ma J.-A. Angew. Chem. Int. Ed. 2011; 50: 3538
- 8h Luo R. Li K. Hu Y. Tang W. Adv. Synth. Catal. 2013; 355: 1297
- 9a Bandini M. Sinisi R. Umani-Ronchi A. Chem. Commun. 2008; 4360
- 9b Enders D. Henseler A. Adv. Synth. Catal. 2009; 351: 1749
- 9c Enders D. Henseler A. Lowins S. Synthesis 2009; 4125
- 9d Wang X.-N. Shao P.-L. Lv H. Ye S. Org. Lett. 2009; 11: 4029
- 9e Enders D. Grossmann A. Fronert J. Raabe G. Chem. Commun. 2010; 46: 6282
- 9f Palacio C. Connon SJ. Org. Lett. 2011; 13: 1298
- 9g Hara N. Tamura R. Funahashi Y. Nakamura S. Org. Lett. 2011; 13: 1662
- 9h Chen X. Yang S. Song B.-A. Chi YR. Angew. Chem. Int. Ed. 2013; 52: 11134
- 9i Lin J. Kang T. Liu Q. He L. Tetrahedron: Asymmetry 2014; 25: 949
- 9j Jing Z. Bai X. Chen W. Zhang G. Zhu B. Jiang Z. Org. Lett. 2016; 18: 260
- 10a Davis JP. Cain GA. Pitts WJ. Magolda RL. Copeland RA. Biochemistry 1996; 35: 1270
- 10b Brough PA. Aherne W. Barril X. Borgognoni J. Boxall K. Cansfield JE. Cheung K.-MJ. Collins I. Davies NG. M. Drysdale MJ. Dymock B. Eccles SA. Finch H. Fink A. Hayes A. Howes R. Hubbard RE. James K. Jordan AM. Lockie A. Martins V. Massey A. Matthews TP. McDonald E. Northfield CJ. Pearl LH. Prodromou C. Ray S. Raynaud FI. Roughley SD. Sharp SY. Surgenor A. Walmsley DL. Webb P. Wood M. Workman P. Wright L. J. Med. Chem. 2008; 51: 196
- 10c Andrzejak V. Muccioli GG. Body-Malapel M. El Bakali J. Djouina M. Renault N. Chavatte P. Desreumaux P. Lambert DM. Millet R. Bioorg. Med. Chem. 2011; 19: 3777
- 10d Kaur K. Kumar V. Sharma AK. Gupta GK. Eur. J. Med. Chem. 2014; 77: 121
- 11 Zhang Y. Wei B. Lin H. Cui W. Zeng X. Fan X. Adv. Synth. Catal. 2015; 357: 1299
- 12 Zhang Y. Wei B.-W. Zou L.-N. Kang M.-L. Luo H.-Q. Fan X.-L. Tetrahedron 2016; 72: 2472
- 13a Taylor MS. Jacobsen EN. Angew. Chem. Int. Ed. 2006; 45: 1520
- 13b Chauhan P. Mahajan S. Kaya U. Hack D. Enders D. Adv. Synth. Catal. 2015; 357: 253
- 14 CCDC 1571220 (3g) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
- 15 Vakulya B. Varga S. Csámpai A. Soós T. Org. Lett. 2005; 7: 1967