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 2020; 52(23): 3650-3656
DOI: 10.1055/s-0040-1706423
DOI: 10.1055/s-0040-1706423
paper
Divergent and Diastereoselective Synthesis of α-Monosubstituted and trans-α,β-Disubstituted γ-Lactams from (S)-N,N-Dibenzyl-α-amino Aldehydes via Henry and Michael Reactions
Weitere Informationen
Publikationsverlauf
Received: 07. Juli 2020
Accepted after revision: 20. Juli 2020
Publikationsdatum:
24. August 2020 (online)
Abstract
γ-Monosubstituted and trans-α,β-disubstituted γ-lactams were diastereoselectively synthesized from common intermediates (S)-N,N-dibenzylated aldehydes derived from natural l-(α)-amino acids, employing a divergent approach. The key features of the routes include diastereoselective Henry and Michael reactions that produced chiral γ-nitroester derivatives, which were subsequently submitted to a tandem reduction-lactamization sequence providing the title compounds. The versatility of routes can allow the preparation of several other mono-, di-, or tri-substituted γ-lactams.
Key words
divergent synthesis - Michael addition - Henry reaction - γ-lactams - domino reaction - diastereoselective synthesis - 1,3-dicarbonyl compoundsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706432.
- Supporting Information
-
References
- 1a Caruano J, Mucciolib GG, Robiette R. Org. Biomol. Chem. 2016; 14: 10134
- 1b Nay B, Riache N, Evanno L. Nat. Prod. Rep. 2009; 26: 1044
- 1c Wei B, Li K-W, Wu Y-C, Tong S-Q, Song R-J. Synthesis 2020; 52: in press; DOI: 10.1055/s-0040-1707835
- 1d Rivas F, Ling T. Org. Prep. Proced. Int. 2016; 48: 254
- 1e Martelli G, Monsignori A, Orena M, Rinaldi S. Curr. Org. Chem. 2014; 18: 1539
- 1f Meazza M, Companyó X, Rios R. Asian J. Org. Chem. 2018; 7: 1934
- 1g Martinez de Marigorta E, de los Santos J, Ochoa de Retana AM, Vicario J, Palacios F. Synthesis 2018; 50: 4539
- 1h Martinez de Marigorta E, de los Santos J, Ochoa de Retana AM, Vicario J, Palacios F. Beilstein J. Org. Chem. 2019; 150: 1065
- 1i Lorenc C, Vibbert HB, Yao C, Norton JR, Rauch M. ACS Catal. 2019; 9: 10294
- 2a Barbaro P, Liguori F, Oldani C, Moreno-Marrodán C. Adv. Sustainable Syst. 2020; 5: 1900117
- 2b Moreno-Marrodan C, Liguori F, Barbaro P. Mol. Catal. 2019; 466: 60
- 2c Jouyban A, Fakhree MA. A, Shayanfar A. J. Pharm. Pharmaceut. Sci. 2010; 13: 524
- 2d Ring-Opening Polymerization of Cyclic Amides (Lactams) . In Polymer Science: A Comprehensive Reference, Vol. 4. Russo S, Casazza E, Penczek S, Grubbs R. Elsevier; Amsterdam: 2013: 331-396
- 3a Manam RR, Teisan S, White DJ, Nicholson B, Grodberg J, Neuteboom ST. C, Lam KS, Mosca DA, Lloyd GK, Potts BC. M. J. Nat. Prod. 2005; 68: 240
- 3b Ko K, Lee S.-H, Kim S.-H, Kim E.-H, Oh K.-B, Shin J, Oh D.-C. J. Nat. Prod. 2014; 77: 2099
- 4a Lin W.-H, Ye Y, Xu R.-S. J. Nat. Prod. 1992; 55: 571
- 4b Wang Y.-Z, Tang C.-P, Dien P.-H, Ye Y. J. Nat. Prod. 2007; 70: 1356
- 4c Yoritate M, Takahashi Y, Tajima H, Ogihara C, Yokoyama T, Soda Y, Oishi T, Sato T, Chida N. J. Am. Chem. Soc. 2017; 139: 18386
- 5 Li JY, Strobel G, Harper J, Lobkovsky E, Clardy J. Org. Lett. 2000; 2: 767
- 6 Lyseng-Williamson KA. Drugs 2011; 71: 489
- 7 Dineva S, Uzunova K, Pavlova V, Filipova E, Kalinov K, Vekov T. J. Hum. Hypertens. 2019; 33: 766
- 8 Wei J, Shaw JT. Org. Lett. 2007; 9: 4077
- 9 Soleimani-Amiri S, Vessally E, Babazadeh M, Hosseiniand A, Edjlalic L. RSC Adv. 2017; 7: 28407
- 10 Park J.-H, Ha J.-R, Oh S.-J, Kim J.-A, Shin D.-S, Won T.-J, Lam Y.-F, Ahn C. Tetrahedron Lett. 2005; 46: 1755
- 11 Peng X, Wang H.-H, Cao F, Zhang H.-H, Lu Y.-M, Hu X.-L, Tan W, Wang Z. Org. Chem. Front. 2019; 6: 1837
- 12 Hong SY, Park Y, Hwang Y, Kim YB, Baik M.-H, Chang S. Science 2018; 359: 1016
- 13 Ye L-W, Shu C, Gagosz F. Org. Biomol. Chem. 2014; 12: 1833
- 14 Gondal HM, Buisson D. Chem. Heterocycl. Comp. 2016; 52: 183
- 15 Borja-Miranda A, Sánchez-Chávez AC, Polindara-García LA. Eur. J. Org. Chem. 2019; 2453
- 16 Luzzio FA. Tetrahedron 2001; 57: 915
- 17 Palomo C, Oiarbide M, Mielgo A. Angew. Chem. Int. Ed. 2004; 43: 5442
- 18 Boruwa J, Gogoi N, Saikia PP, Barua NC. Tetrahedron: Asymmetry 2006; 17: 3315
- 19 Palomo C, Oiarbide M, Laso A. Eur. J. Org. Chem. 2007; 2561
- 20 Dong L, Chen F-E. RSC Adv. 2020; 10: 2313
- 21 Singh N, Pandey J. Mini-Rev. Org. Chem. 2020; 17: 297
- 22 Zhang S, Li Y, Xu Y, Wang Z. Chin. Chem. Let. 2018; 29: 873
- 23 Sappino C, Primitivo L, De Angelis M, Domenici MO, Mastrodonato A, Romdan IB, Tatangelo C, Suber L, Pilloni L, Ricelli A, Righi G. ACS Omega 2019; 4: 21809
- 24 Reznikov AN, Klimochkin YN. Synthesis 2020; 52: 781
- 25 Li Y, Yu J, Bi Y, Yan G, Huang D. Adv. Synth. Catal. 2019; 361: 4839
- 26 Ballini R, Bosica G, Fiorini D, Palmieri A, Petrini M. Chem. Rev. 2005; 105: 933
- 27 Turova MG, Sergeio OG, Zlotin SG. Org. Biomol. Chem. 2019; 17: 3670
- 28 Pellissier H. Curr. Org. Chem. 2018; 22: 323
- 29 Byrd KM. Beilstein J. Org. Chem. 2015; 11: 530
- 30 Zheng K, Liu X, Feng X. Chem. Rev. 2018; 118: 7586
- 31 Pereira VL. P, Moura AL. S, Vieira DP. P, Carvalho LL, Torres ER. B, Costa JS. Beilstein J. Org. Chem. 2013; 9: 832
- 32 de Carvalho LL, Burrow RA, Pereira VL. P. Beilstein J. Org. Chem. 2013; 9: 838
- 33 Barreto CB. Jr, Pereira VL. P. Tetrahedron Lett. 2009; 50: 6389
- 34 Pennaforte EV, Costa JS, Silva CA, Saraiva MC, Pereira VL. P. Parte superior do formulárioLett. Org. Chem. 2009; 6: 110
- 35 Costa JS, Freire BS, Moura AL. S, Pereira VL. P. J. Braz. Chem. Soc. 2006; 17: 1229
- 36 Pinto AC, Freitas CB. L, Dias AG, Pereira VL. P, Tinant B, Declercq J.-P, Costa PR. R. Tetrahedron: Asymmetry 2002; 13: 1025
- 37 Silva PC, Costa JS, Pereira VL. P. Synth. Commun. 2001; 31: 595
- 38 Costa JS, Dias AG, Anholeto AL, Monteiro MD, Patrocinio VL, Costa PR. R. J. Org. Chem. 1997; 62: 4002
- 39 Patrocinio VL, Costa PR. R, Correia CR. D. Synthesis 1994; 474
- 40 Reetz MT. Chem. Rev. 1999; 99: 1121
- 41 Reetz MT, Drewes MW, Schwickardi R. Org. Synth. Coll. Vol. 10 . Wiley; New York: 2004: 256-262
- 42 Hanessian S, Devasthale PV. Tetrahedron Lett. 1996; 37: 987
- 43 Hynes PS, Stupple PA, Dixon DJ. Org. Lett. 2008; 10: 1389
- 44 Chasar DW. Synthesis 1982; 841
- 45 Drinan MA, Lash TD. J. Heterocycl. Chem. 1994; 31: 255
- 46 Shakirov RR, Yarmukhamedov NN, Vlasova LI, Baibulatova NZ, Khisamutdinova RYu, Gabdrakhmanova SF, Karachurina LT, Baschenko NZh. Pharm. Chem. J. 2006; 40: 29
- 47 Escalante J, Diaz-Coutinho FD. Molecules 2009; 14: 1595
- 48 Ballini R, Bosica G, Forconi P. Tetrahedron 1996; 52: 1677
- 49 Yeom C-E, Kim MJ, Kim BM. Tetrahedron 2007; 63: 904
- 50 Tehri P, Peddinti RK. Org. Biomol. Chem. 2019; 17: 3964
- 51 Fedotova A, Crousse B, Chataigner I, Maddaluno J, Rulev AY, Legros J. J. Org. Chem. 2015; 80: 10375
- 52 Ahn NT, Eisenstein O. Tetrahedron Lett. 1976; 155
- 53 Burgi HB, Dunitz JD, Lehn JM, Wipff G. Tetrahedron 1974; 30: 1563
- 54 Bernardi A, Micheli F, Potenza D, Scolastico C, Villa R. Tetrahedron Lett. 1990; 31: 4949
- 55 Simas AB. C, Pereira VL. P, Barreto CB. Jr, de Sales DL, de Carvalho LL. Quim. Nova 2009; 32: 2473