Asymmetric synthesis of functionalized chromans via a one-pot organocatalytic domino Michael-hemiacetalization or -lactonization and dehydration sequence

Synthesis

Volumn 44, Issue 5, 2012, Pages 773-782

  Enders, Dieter ^a   Urbanietz, Gregor ^a   Hahn, Robert ^a   Raabe, Gerhard ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

chromans; domino reaction; one pot reaction; organocatalysis; thiourea

Indexed keywords

ASYMMETRIC SYNTHESIS; CHROMAN DERIVATIVES; CHROMANS; CHROMENES; DOMINO REACTIONS; ENANTIOSELECTIVE SYNTHESIS; FUNCTIONALIZED; LACTONIZATION; ONE POT; ONE-POT REACTION; ORGANOCATALYSIS; ORGANOCATALYTIC;

CATALYSIS; DEHYDRATION; DEWATERING; FUNCTIONAL GROUPS; PHENOLS; REACTION KINETICS; THIOUREAS;

ENANTIOSELECTIVITY;

2 ETHYLIDENE 4 (NITROMETHYL)SPIRO(CHROMAN 3,1' CYCLOPENTAN) 2' ONE; 2 METHYLENE 4 (NITROMETHYL)SPIRO(CHROMAN 3,1' CYCLOPENTAN) 2' ONE; 3,3 DIMETHYL 9 (NITROMETHYL) 2,3,4,9 TETRAHYDRO 1H XANTHEN 1 ONE; 4 (NITROMETHYL)SPIRO(CHROMAN 3,1' CYCLOPENTANE) 2,2' DIONE; 9 (NITROMETHYL) 2,3 DIHYDROCYCLOPENTA[B]CHROMEN 1(9H) ONE; 9 (NITROMETHYL) 2,3,4,9 TETRAHYDRO 1H XANTHEN 1 ONE; CHROMAN DERIVATIVE; ETHYL 9 (NITROMETHYL) 1,2,9,9A TETRAHYDROCYCLOPENTA[B]CHROMENE 9A CARBOXYLATE; ETHYL 9 (NITROMETHYL) 2,3,9,9A TETRAHYDRO 1H XANTHENE 9A CARBOXYLATE; METHYL 1 [1 (2 HYDROXYPHENYL) 2 NITROETHYL] 2 OXOCYCLOPENTANECARBOXYLATE; METHYL 3A HYDROXY 9 (NITROMETHYL) 1,2,3,3A,9,9A HEXAHYDROCYCLOPENTA[B]CHROMENE 9A CARBOXYLATE; METHYL 3A METHOXY 9 (NITROMETHYL) 1,2,3,3A,9,9A HEXAHYDROCYCLOPENTA[B]CHROMENE 9A CARBOXYLATE; METHYL 5 METHOXY 9 (NITROMETHYL) 1,2,9,9A TETRAHYDROCYCLOPENTA[B]CHROMENE 9A CARBOXYLATE; METHYL 6 METHYL 9 (NITROMETHYL) 1,2,9,9A TETRAHYDROCYCLOPENTA[B]CHROMENE 9A CARBOXYLATE; METHYL 7 BROMO 5 METHOXY 9 (NITROMETHYL) 1,2,9,9A TETRAHYDROCYCLOPENTA[B]CHROMENE 9A CARBOXYLATE; METHYL 7 BROMO 9 (NITROMETHYL) 1,2,9,9A TETRAHYDROCYCLOPENTA[B]CHROMENE 9A CARBOXYLATE; METHYL 9 (NITROMETHYL) 1,2,3,3A,9,9A HEXAHYDROCYCLOPENTA[B]CHROMENE 9A CARBOXYLATE; METHYL 9 (NITROMETHYL) 1,2,9,9A TETRAHYDROCYCLOPENTA[B]CHROMENE 9A CARBOXYLATE; METHYL 9 (NITROMETHYL) 2,3,9,9A TETRAHYDRO 1H XANTHENE 9A CARBOXYLATE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DOMINO MICHAEL HEMIACETALIZATION AND DEHYDRATION SEQUENCE; DOMINO MICHAEL LACTONIZATION REACTION; ENVIRONMENTAL TEMPERATURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LACTONIZATION; NUCLEOPHILICITY; PROCESS OPTIMIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 84857455190     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0031-1289683     Document Type: Article

References (36)

1. For reviews on organocatalytic domino reactions, see:, Grossmann A, Enders D, Angew. Chem. Int. Ed. 2012 51 314
2. Pellissier H, Adv. Synth. Catal. 2012 354 in press
3. Enders D, Jeanty M, Grondal C, Nat. Chem. 2010 2 167
4. Alba A.-N, Companyo X, Viciano M, Rios R, Curr. Org. Chem. 2009 13 1432
5. Yu X, Wang W, Org. Biomol. Chem. 2008 6 2037
6. Enders D, Grondal C, Hüttl M R. M., Angew. Chem. Int. Ed. 2007 46 1570
7. For recent examples of organocatalytic asymmetric syntheses of chromans, see:, Enders D, Yang X, Wang C, Raabe G, Runsink J, Chem. Asian J. 2011 6 2255
8. Enders D, Urbanietz G, Raabe G, Synthesis 2011 1905
9. Hong B C., Kotame P, Liao J.-H, Org. Biomol. Chem. 2011 9 382
10. Ren Q, Siau W.-Y, Du Z, Zhang K, Wang J, Chem. Eur. J. 2011 17 778
11. Hong B C., Kotame P, Lee G.-H, Org. Lett. 2011 13 5758
12. Lee Y, Seo S W., Kim S.-G, Adv. Synth. Catal. 2011 353 2671
13. Zhang X, Zhang S, Wang W, Angew. Chem. Int. Ed. 2010 49 1481
14. Alemán J, Nuez A, Marzo L, Marcos V, Alvarado C, Ruano J L. G., Eur. J. Org. Chem. 2010 16 9453
15. Lu D, Li Y, Gong Y, J. Org. Chem. 2010 75 6900
16. Ramachary D B., Sakthidevi R, Org. Biomol. Chem. 2010 8 4259
17. Manzano R, Andrés J M., Muruzábal M D., Pedrosa R, Adv. Synth. Catal. 2010 352 3364
18. Enders D, Wang C, Yang X, Raabe G, Adv. Synth. Catal. 2010 352 2869
19. Shen H C., Tetrahedron 2009 65 3931
20. Ferreira S B., da Silva F de C, Pinto A C., Gonzaga D T. G., Ferreira V F., J. Heterocycl. Chem. 2009 46 1080
21. Deiters A, Martin S F., Chem. Rev. 2004 104 2199
22. Nicolaou K C., Pfefferkorn J A., Roecker A J., Cao G.-Q, Barluenga S, Mitchell H J., J. Am. Chem. Soc. 2000 122 9939
23. Keay B A., In Comprehensive Heterocyclic Chemistry II Vol. 2 Pergamon Oxford 1996
24. Schweizer E E., Meeder-Nycz O, In Chromenes, Chromans, Chromones Ellis G P. Wiley-Interscience New York 1977
25. For examples of organocatalytic asymmetric Michael-hemiacetalization reactions, see:, Wang Y, Zhu S, Ma D, Org. Lett. 2011 13 1602
26. Ishikawa H, Sawano S, Yasui Y, Shibata Y, Hayashi Y, Angew. Chem. Int. Ed. 2011 50 3774
27. Belot S, Quintard A, Alexakis A, Krause N, Adv. Synth. Catal. 2010 352 667
28. Maltsev O V., Kucherenko A S., Zlotin S G., Chimishkyan A L., Tetrahedron: Asymmetry 2010 21 2659
29. Yao W, Wu Y, Wang G, Zhang Y, Cheng M, Angew. Chem. Int. Ed. 2009 48 9713
30. Chandrasekhar S, Mallikarjun K, Pavankumarreddy G, Rao K V., Jagadeesh B, Chem. Commun. 2009 4985
31. Wang J, Yu F, Zhang X, Ma D, Org. Lett. 2008 10 2561
32. Xie J W., Uang X, Fan L P., Xu D C., Li X S., Su H, Wen Y H., Adv. Synth. Catal. 2008 350 1474
33. 4OAc according to the literature procedure:, Zhang B.-L, Wang F.-D, Yue J.-M, Synlett 2006 567
34. Okino T, YasutakaHoashi Y, Takemoto Y, J. Am. Chem. Soc. 2003 125 12672
35. Vakulya B, Varga S, Csampai A, Soos T, Org. Lett. 2005 7 1967
36. CCDC 859260 contains the supplementary crystallographic data of 5d for this paper. These data can be obtained free of charge from The CambridgeCrystallographicDataCentre via www.ccdc.cam.ac.uk/data-request/cif.