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Synthesis 2015; 47(23): 3776-3782
DOI: 10.1055/s-0035-1560088
DOI: 10.1055/s-0035-1560088
paper
Racemization-Free Synthesis of Morpholinone Derivatives from α-Amino Acids
Authors
Weitere Informationen
Publikationsverlauf
Received: 12. Mai 2015
Accepted after revision: 11. Juli 2015
Publikationsdatum:
25. August 2015 (online)
Abstract
A simple strategy is reported for the synthesis of chiral N-protected morpholinone derivatives by a base (potassium carbonate)-mediated cyclization reaction of N-protected α-amino acids with 1,2-dibromoethane. The morpholinone derivatives are obtained in good yields and in enantiomerically pure forms.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1560088.
- Supporting Information (PDF)
-
References
- 1 Wijtmans R, Vink MK. S, Schoemaker HE, van Delft FL, Blaauw RH, Rutjes FP. J. T. Synthesis 2004; 641 ; and references therein
- 2a Grinsteiner TJ, Kishi Y. Tetrahedron Lett. 1994; 35: 8333
- 2b Grinsteiner TJ, Kishi Y. Tetrahedron Lett. 1994; 35: 8337
- 2c Clark SM, Osborn HM. I. Tetrahedron: Asymmetry 2004; 15: 3643
- 2d Yar M, McGarrigle EM, Aggarwal VK. Org. Lett. 2009; 11: 257
- 2e Hajós M, Fleishaker JC, Filipiak-Reisner JK, Brown MT, Wong EH. F. CNS Drug Rev. 2004; 10: 23
- 2f Versiani M, Cassano G, Perugi G, Benedetti A, Mastalli L, Nardi A, Savino M. J. Clin. Psychiatry 2002; 63: 31
- 2g Wong EH. F, Sonders MS, Amara SG, Tinholt PM, Piercey MF. P, Hoffmann WP, Hyslop DK, Franklin S, Porsolt RD, Bonsignori A, Carfagna N, McArthur RA. Biol. Psychiatry 2000; 47: 818
- 2h Pendergrass K, Hargreaves R, Petty KJ, Carides AD, Evans JK, Horgan KJ. Drugs Today 2004; 40: 853
- 2i Hikichi M, Yokokura T, Furuta T, Yaegashi T. JP 62135472, 1987 ; Chem. Abstr. 1987, 107, 198358
- 2j Gharpure JS, Prasad KV. J. J. Org. Chem. 2011; 76: 10325
- 3a Nilsson JW, Kvarnström I, Musil D, Nilsson I, Samuelsson B. J. Med. Chem. 2003; 46: 3985
- 3b Gonzalez AZ, Eksterowicz J, Bartberger MD, Beck HP, Canon J, Chen A, Chow D, Duquette J, Fox BM, Fu J, Huang X, Houze JB, Jin L, Li Y, Li Z, Ling Y, Lo M.-C, Long AM, McGee LR, McIntosh J, McMinn DL, Oliner JD, Osgood T, Rew Y, Saiki AY, Shaffer P, Wortman S, Yakowec P, Yan X, Ye Q, Yu D, Zhao X, Zhou J, Olson SH, Medina JC, Sun D. J. Med. Chem. 2014; 57: 2472
- 4a Dave R, Sasaki NA. Org. Lett. 2004; 6: 15
- 4b Dave R, Sasaki NA. Tetrahedron: Asymmetry 2006; 17: 388
- 4c Bettoni G, Frachini C, Perrone P, Tortorella V. Tetrahedron 1980; 36: 409
- 4d Sladojevich F, Trabocchi A, Guarna A. J. Org. Chem. 2007; 72: 4254
- 5a Breuning M, Winnacker M, Steiner M. Eur. J. Org. Chem. 2007; 2100
- 5b Lanman BA, Myers AG. Org. Lett. 2004; 6: 1045
- 5c Métro T.-X, Pardo DG, Cossy J. J. Org. Chem. 2008; 73: 707
- 5d Brenner E, Baldwin RM, Tamagnan G. Org. Lett. 2005; 7: 937
- 5e Cupples CA, Morton HN. WO 9638465, 1996
- 5f Fish PV, Mackenny M, Bish G, Buxton T, Cave R, Drouard D, Hoople D, Jessiman A, Miller D, Pasquinet C, Patel B, Reeves K, Ryckmans T, Skerten M, Wakenhut F. Tetrahedron Lett. 2009; 50: 389
- 6a Albanese D, Salsa M, Landini D, Lupi V, Penso M. Eur. J. Org. Chem. 2007; 2107
- 6b Abdel-Jalil RJ, Ali Shah ST, Khan KM, Voelter W. Lett. Org. Chem. 2005; 2: 306
- 6c Henegar KE. J. Org. Chem. 2008; 73: 3662
- 6d Lupi V, Albanese D, Landini D, Scaletti D, Penso M. Tetrahedron 2004; 60: 11709
- 7a Ghorai MK, Shukla D, Bhattacharyya A. J. Org. Chem. 2012; 77: 3740
- 7b Ghorai MK, Shukla D, Das K. J. Org. Chem. 2009; 74: 7013
- 7c Wang L, Liu Q.-B, Wang D.-S, Li X, Han X.-W, Xiao W.-J, Zhou Y.-G. Org. Lett. 2009; 11: 1119
- 7d Bera M, Roy S. J. Org. Chem. 2009; 74: 8814
- 7e D’hooghe M, Vanlangendonck T, Törnroos KW, De Kimpe N. J. Org. Chem. 2006; 71: 4678
- 7f Taylor AM, Schreiber SL. Tetrahedron Lett. 2009; 50: 3230
- 7g Kogami Y, Okawa K. Bull. Chem. Soc. Jpn. 1987; 60: 2963
- 7h Mollet K, Goossens H, Piens N, Catak S, Waroquier M, Törnroos KW, Van Speybroeck V, D’hooghe M, De Kimpe N. Chem. Eur. J. 2013; 19: 3383
- 8a Siddiqui SA, Narkhede UC, Lahoti RJ, Srinivasan KV. Synlett 2006; 1771
- 8b Nishi T, Ishibashi K, Nakajima K, Iio Y, Fukuzawa T. Tetrahedron: Asymmetry 1998; 9: 3251
- 8c Takemoto T, Iio Y, Nishi T. Tetrahedron Lett. 2000; 41: 1785
- 8d D’Arrigo P, Lattanzio M, Pedrocchi G, Servi S. Tetrahedron: Asymmetry 1998; 9: 4021
- 8e Wilkinson MC. Tetrahedron Lett. 2005; 46: 4773
- 9a Grotenberg GM, Christina AE, Buizert AE. M, van der Marel GA, Overkleeft HS, Overhand M. J. Org. Chem. 2004; 69: 8331
- 9b Du M, Hindsgaul O. Synlett 1997; 395
- 10 Yar M, McGarrigle EM, Aggarwal VK. Angew. Chem. Int. Ed. 2008; 47: 3784
- 11 Ritzen B, Hoekman S, Duràn Verdasco E, van Delft FL, Rutjes FP. J. T. J. Org. Chem. 2010; 75: 3461
- 12a Pedrosa R, Andrés C, Mendiguchia P, Nieto J. J. Org. Chem. 2006; 71: 8854
- 12b Yamazaki A, Achiwa K. Tetrahedron: Asymmetry 1995; 6: 1021
- 13 Kasima C, Harada K. J. Chem. Soc., Perkin Trans. 1 1988; 1521
- 14a Devine PN, Foster BS, Grabowski EJ. J, Reider PJ. Heterocycles 2002; 58: 119
- 14b Park YS, Lee YM, Kang KH, Min HM, Lim HJ, Park EH. ARKIVOC 2010; (ii): 1
- 15 Baek J, Jang JI, Park YS. Bull. Korean Chem. Soc. 2011; 32: 4067
- 16 Burdzhiev N, Stanoeva E, Shivachev B, Nikolova R. C. R. Chim. 2014; 17: 420
- 17a Samanta S, Bhattacharyya A, Das S, Ghorai MK. Curr. Org. Chem. 2014; 18: 2842
- 17b Talukdar R, Tiwari DP, Saha A, Ghorai MK. Org. Lett. 2014; 16: 3954
- 17c Ghorai MK, Samanta S, Das S. Asian J. Org. Chem. 2013; 2: 1026
- 18a Ghorai MK, Nanaji Y, Yadav AK. Org. Lett. 2011; 13: 4256
- 18b Ghorai MK, Das K, Kumar A. Tetrahedron Lett. 2007; 48: 4373
- 18c Ghorai MK, Ghosh K. Tetrahedron Lett. 2007; 48: 3191
- 18d Ghorai MK, Das K, Kumar A. Tetrahedron Lett. 2009; 50: 1105
- 18e Ghorai MK, Das K, Kumar A, Ghosh K. Tetrahedron Lett. 2005; 46: 4103
- 18f Ghorai MK, Das K, Kumar A, Das A. Tetrahedron Lett. 2006; 47: 5393
- 18g Ghorai MK, Sahoo AK, Kumar S. Org. Lett. 2011; 13: 5972
- 18h Ghorai MK, Halder S, Samanta S. Aust. J. Chem. 2012; 65: 1262
- 18i Ghorai MK, Halder S, Das RK. J. Org. Chem. 2010; 75: 7061
- 19 The ee of morpholinone 2b (>99%), as a representative example of morpholinones 2a–f, was determined by chiral HPLC analysis.
- 20 See the Supporting Information for details.
- 21 Crystallographic data for compounds 2a and 2b have been deposited with the accession numbers CCDC 1033183 and 1033184, respectively, and can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk; Web site: www.ccdc.cam.ac.uk/conts/retrieving.html.
- 22 The ee of morpholine 9a (>99%), as a representative example of morpholines 9a and 9b, was determined by chiral HPLC analysis.
- 23 The ee of morpholine 11a (>99%), as a representative example of morpholines 11a–d, was determined by chiral HPLC analysis.