Diastereocontrol in the synthesis of 2,3,4-trisubstituted pyrrolidines and tetrahydrofurans via a palladium(II)-catalyzed three-component coupling reaction

Synthesis (Germany)

Volumn 44, Issue 13, 2012, Pages 1983-1992

  Raikar, Sandeep ^a   Pal, Benoy Kumar ^a   Malinakova, Helena C ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

heterocycles; multicomponent reactions; palladium; ring closure; stereoselective synthesis

Indexed keywords

ALLENES; ASSIGNMENT OF; BORONIC ACID; COMBINATORIAL LIBRARY; DIASTEREOCONTROL; HETEROCYCLES; MULTI-COMPONENT REACTIONS; NATURAL PRODUCTS; PALLADIUM-CATALYZED; PHARMACEUTICAL AGENTS; PYRROLIDINES; RING CLOSURES; STEREOSELECTIVE SYNTHESIS; TETRAHYDROFURANS; THREE-COMPONENT COUPLING REACTION;

ALDEHYDES; CATALYSIS; HYDROCARBONS; PALLADIUM; STEREOCHEMISTRY; STEREOSELECTIVITY;

PALLADIUM COMPOUNDS;

2 (2 FURYL) 3 (1 HEXYL) 4 (4 METHOXYPHENYL)TETRAHYDROFURAN; 2 (ETHOXYCARBONYL) 3 HEXYL 4 PHENYL 1 TOSYLPYRROLIDONE; 3 (2 ETHYLHEXYL) 2,4 BIS[4 (METHOXYCARBONYL)PHENYL] 1 TOSYLPYRROLIDINE; 3 HEXYL 2 [4 (METHOXYCARBONYL)PHENYL] 4 (2 NAPHTHYL) 1 TOSYLPYRROLIDINE; 3 HEXYL 2,4 (4 METHOXYPHENYL)TETRAHYDROFURAN; 3 HEXYL 2,4 BIS[4 (METHOXYCARBONYL)PHENYL] 1 TOSYLPYRROLIDINE; 3 HEXYL 4 (4 METHOXYPHENYL) 2 (4 NITROPHENYL)TETRAHYDROFURAN; 3 HEXYL 4 (4 METHOXYPHENYL) 2 PHENYLTETRAHYDROFURAN; 3 HEXYL 4 [4 (METHOXYCARBONYL)PHENYL] 2 (4 NITROPHENYL) 1 TOSYLPYRROLIDINE; ALDEHYDE DERIVATIVE; ALLENE DERIVATIVE; BORONIC ACID DERIVATIVE; IMINE; PALLADIUM; PYRROLIDINE DERIVATIVE; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; METHODOLOGY; STEREOCHEMISTRY; SYNTHESIS;

EID: 84862768929     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0031-1290969     Document Type: Article

References (34)

1. Jae H.-S, Winn M, von Geldern TW, Sorensen BK, Chiou WJ, Nguyen B, Marsh KC, Opgenorth TJ. J. Med. Chem.: 2001; 44 3978
2. Yang B.-H, Zhang W.-D, Liu R.-H, Li T.-Z, Zhang C, Zhou Y, Su J. J. Nat. Prod.: 2005; 68 1175
3. Lin SL, Liu X.-H, Shen Y.-H, Li H.-L, Shan L, Liu R.-H, Xu X.-K, Zhang W.-D, Wang H. J. Nat. Prod.: 2010; 73 632
4. Chen C, Li X, Schreiber SL. J. Am. Chem. Soc.: 2003; 125 10174
5. Scott ME, Han W, Lautens M. Org. Lett.: 2004; 6 3309
6. Pohlhaus PD, Sanders SD, Parsons AT, Li W, Johnson JS. J. Am. Chem. Soc.: 2008; 130 8642
7. Chaulagain MR, Aron ZD. J. Org. Chem.: 2010; 75 8271
8. Bueno ND, Jimenez A, Pedregal C, Vidal P. Tetrahedron Lett.: 2006; 17 2489
9. Yazici A, Pyne SG. Synthesis: 2009; 513
10. Peixoto S, Nguyen TM, Crich D, Delpech B, Marazano C. Org. Lett.: 2010; 12 4760
11. Paderes MC, Chemler SR. Org. Lett.: 2009; 11 1915
12. Komsta Z, Barbasiewicz M, Makosza M. J. Org. Chem.: 2010; 75 3251
13. Zhou L, Chen J, Tan CK, Yeung Y.-Y. J. Am. Chem. Soc.: 2011; 133 9164
14. Kotland A, Accadbled F, Robeyns K, Behr J.-B. J. Org. Chem.: 2011; 76 4094
15. Hopkins CD, Malinakova HC. Org. Lett.: 2006; 8 5971
16. Hopkins CD, Malinakova HC. Synthesis: 2007; 3558
17. Murphy MM, Schullek JR, Gordon EM, Gallop MA. J. Am. Chem. Soc.: 1995; 117 7029
18. Kumar A, Gupta G, Srivastava S. J. Comb. Chem.: 2010; 12 458
19. Liu H, Dou G, Shi D. J. Comb. Chem.: 2010; 12 292
20. An H, Cook PD. Chem. Rev.: 2000; 100 3311
21. Sunderhaus JD, Martin SF. Chem.-Eur. J.: 2009; 15 1300
22. Ganem B. Acc. Chem. Res.: 2009; 42 463
23. See also ref. 4d
24. Kronenthal DR, Han CY, Taylor MK. J. Org. Chem.: 1982; 47 2765
25. Hasegawa M, Taniyama D, Tomioka K. Tetrahedron: 2000; 56 10153
26. Overman LE, Owen CE, Pavan MM. Org. Lett.: 2003; 5 1809
27. Hata S, Iguchi M, Iwasawa T, Yamada K.-I, Tomioka K. Org. Lett.: 2004; 6 1721
28. Marin SD. L, Martens T, Mioskowski C, Royer J. J. Org. Chem.: 2005; 70 10592
29. Maligres PE, Waters MM, Lee J, Reamer RA, Askin D, Ashwood MS, Cameron M. J. Org. Chem.: 2002; 67 1093
30. Sajjadi Z, Lubell WD. J. Pept. Res.: 2005; 65 298
31. Still WC, Barrish JC. J. Am. Chem. Soc.: 1983; 105 2487
32. Loiseleur O, Koch G, Wagner T. Org. Process Res. Dev.: 2004; 8 597
33. Houk KN, Rondan NG, Wu YD, Metz JT, Paddon-Row MN. Tetrahedron: 1984; 40 2257
34. Hoffmann RW. Chem. Rev.: 1989; 89 1841