Three-component, diastereoselective synthesis of highly functionalized indane derivatives based on an anionic domino sequence from α-nitroketones

Synlett

Volumn , Issue 16, 2010, Pages 2465-2467

  Giorgi, Giorgio ^a   Arroyo, Francisco J ^a   López Alvarado, Pilar ^a   Menéndez, J Carlos ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

carbanions; carbocycles; domino reactions; nitroaldol reactions; nitroketones

Indexed keywords

1,2 DIALDEHYDE DERIVATIVE; 2 NITROINDANE 1,2 DIOL DERIVATIVE; ALDEHYDE DERIVATIVE; ALPHA NITROKETONE DERIVATIVE; HYDROXYL GROUP; INDAN DERIVATIVE; KETONE DERIVATIVE; TETRAHYDROFURAN; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 77957163833     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1258048     Document Type: Article

References (23)

1. For selected reviews of diversity-oriented synthesis, see:, Burke M D., Schreiber S L., Angew. Chem. Int. Ed. 2004 43 46
2. Tan D S., Nature Chem. Biol. 2005 1 74
3. Spandl R J., Bender A, Spring R D., Org. Biomol. Chem. 2008 6 1149
4. For selected reviews of domino reactions, see:, Tietze L F., Beifuss U, Angew. Chem., Int. Ed. Engl. 1993 32 131
5. Tietze L F., Chem. Rev. 1996 96 115
6. Rodriguez J, Synlett 1999 505
7. Pellisier H, Tetrahedron 2006 62 1619
8. Pellisier H, Tetrahedron 2006 62 2143
9. Liéby-Muller F, Simon C, Constantieux T, Rodriguez J, Padwa A, Adv. Heterocycl. Chem. 2007 94 1
10. For a monograph, see:, Padwa A, Bur S K., Tetrahedron 2007 63 5341
11. Tietze L F., Brasche G, Gericke K M., Domino Reactions in Organic Synthesis Wiley-VCH Weinheim 2006
12. For a review, see:, Nicolaou K C., Edmonds D J., Bulger P G., Angew. Chem. Int. Ed. 2006 45 7134
13. Miranda S, López-Alvarado P, Giorgi G, Rodríguez J, Avenda?o C, Menéndez J C., Synlett 2003 2159
14. Giorgi G, Miranda S, López-Alvarado P, Avenda?o C, Rodríguez J, Menéndez J C., Org. Lett. 2005 7 2197
15. Kesavan S, Panek J S., Porco J A. Jr., Org. Lett. 2007 9 5203
16. For a representative example, see:, Ersmark K, Feierberg I, Bjelic S, Hamelink E, Hackett F, Blackman M J., Hulten J.-H, Samuelsson B, Qvist J, Hallberg A, J. Med. Chem. 2004 47 110
17. Fukatsu K, Uchikawa O, Kawada M, Yamano T, Yamashita M, Kato K, Hirai K, Hinuma S, Miyamoto M, Ohkawa S, J. Med. Chem. 2002 45 4212
18. Matsui T, Kondo T, Nishita Y, Itadani S, Tsuruta H, Fujita S, Omawari N, Sakai M, Nakazawa S, Ogata A, Mori H, Kamoshima W, Terai K, Ohno H, Obata T, Nakai H, Toda M, Bioorg. Med. Chem. 2002 10 3787
19. Molteni V, Rhodes D, Rubins K, Hansen M, Bushman F D., Siegel J S., J. Med. Chem. 2000 43 2031
20. See, for instance:, Hett R, Senanayake C H., Wald S A., Tetrahedron Lett. 1998 39 1705
21. Zhao C.-X, Duffey M O., Taylor S J., Morken J P., Org. Lett. 2001 3 1829
22. Farooq O, Synthesis 1994 1035
23. Baer H H., Achmatowicz B, J. Org. Chem. 1964 29 3180