Synthesis of spiroheterocycles by palladium-catalyzed domino cycloisomerization/cross-coupling of α-allenols and Baylis-Hillman acetates

Chemistry - A European Journal

Volumn 15, Issue 14, 2009, Pages 3344-3346

  Alcaide, Benito ^a   Almendros, Pedro ^b   Del Campo, Teresa Martínez ^a   Teresa Quiros M ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

Allenes; Heterocycles; Palladium; Spiro compounds; Synthetic methods

Indexed keywords

CYANIDES; ESTERS; PALLADIUM; REACTION KINETICS; SYNTHESIS (CHEMICAL);

ALLENES; BAYLIS-HILLMAN ACETATES; BENZYLIC; CARBON ATOMS; COUPLING REACTIONS; CYANO GROUPS; DIHYDROFURAN; DOMINO REACTIONS; ENANTIOPURE; FACILE ACCESS; FUNCTIONALIZED; HETEROCYCLES; METHYL ACRYLATES; SPIRO COMPOUNDS; SPIROHETEROCYCLES; SYNTHETIC METHODS;

ORGANOMETALLICS;

EID: 63749122772     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200900096     Document Type: Article

References (47)

1. For selected reviews, see: a) V. Singh, S. Batra, Tetrahedron 2008, 64, 4511;
2. b) D. Basavaiah, K. V. Rao, R. J. Reddy, Chem. Soc. Rev. 2007, 36, 1581;
3. c) D. Basavaiah, A. J. Rao, T. Satyanarayana, Chem. Rev. 2003, 103, 811.
4. For selected reviews, see: a) N. Bongers, N. Krause, Angew. Chem. 2008, 47, 2178:
5. Angew. Chem. Int. Ed. 2008, 120, 2208;
6. b) R. A. Widenhoefer, Chem. Eur. J. 2008, 14, 5382;
7. c) S. Ma, Chem. Rev. 2005, 105, 2829;
8. d) Modern Allene Chemistry (Eds.: N. Krause, A. S. K. Hashmi), Wiley-VCH, Weinheim, 2004;
9. e) R. Zimmer, C. U. Dinesh, E. Nandanan, F. A. Khan, Chem. Rev. 2000, 100, 3067;
10. f) A. S. K. Hashmi, Angew. Chem. 2000, 112, 3737;
11. Angew. Chem. Int. Ed. 2000, 39, 3590.
12. See, for instance: a) B. Alcaide, P. Almendros, T. Martínez del Campo, E. Soriano, J. L. Marco-Contelles. Chem. Eur. J. 2009, 15, 1901;
13. b) B. Alcaide, P. Almendros, T. Martínez del Campo, Chem. Eur. J. 2008, 14, 7756;
14. c) B. Alcaide, P. Almendros, R. Carrascosa, M.C. Redondo, Chem. Eur. J. 2008, 14, 637;
15. d) B. Alcaide, P. Almendros, T. Martínez del Campo, Angew. Chem. 2007, 119, 6804;
16. Angew. Chem. Int. Ed. 2007, 46, 6684;
17. e) B. Alcaide, P. Almendros, T. Martínez del Campo, Angew. Chem. 2006, 118, 4613:
18. Angew. Chem. Int. Ed. 2006, 45, 4501.
19. For 1a, see: a) reference [3e]. For 1b and 1c. see: b) B. Alcaide, P. Almendros, C. Aragoncillo, R. Rodríguez-Acebes, J. Org. Chem. 2001, 66, 5208. For 1d, see:
20. c) B. Alcaide, P. Almendros, R. Rodríguez-Acebes, j. Org. Chem. 2005, 70, 3198.
21. For the homodimeric coupling of 2,3-allenols, see: a) Y. Deng, Y. Yu, S. Ma, J. Org. Chem. 2008, 73, 585. For the Pd-calalyzed cyclizative coupling reaction of α-allenols with allyl halides, see:
22. b) D. Xu, Z. Li, S. Ma, Chem. Eur. J. 2002, 8, 5012.
23. For selected reviews, see: a) K. Ding, Z. Han, Z. Wang, Chem. Asian J. 2009, 4, 32;
24. b) S. Kotha, A. C. Deb. K. Lahiri, E. Manivannan, Synthesis 2009, 165:
25. c) M. Sannigrahi, Tetrahedron 1999, 55, 9007:
26. d) C. H. Heathcock, S. L. Graham, M. C. Pirrung, F. Plavac, C. T. White in Spirocyclic Systems: The Total Synthesis of Natural Products, Vol. 5 (Ed.: j. ApSimon), Wiley, New York, 1983, pp. 264-313.
27. Spiroindolinones exhibit a variety of interesting chemical and biological properties. For selected recent references, see: a) S. Crosignani, P. Page, M. Missotten, V. Colovray, C. Cleva, J.-F. Arrighi, J. Atherall, J. Macritchie, T. Martin, Y. Humbert, M. Gaudet, D. Pupowicz, M. Maio, P.-A. Pittet, L. Golzio, C. Giachetti, C. Rocha, G. Bernardinelli, Y. Filinchuk, A. Scheer, M. K. Schwarz, A. Chollet, J. Med. Chem. 2008, 51, 2227;
28. b) D. M. D'Souza, A. Kiel, D.-P. Herten, F. Rominger, T J. J. Müller, Chem. Eur. J. 2008, 14, 529;
29. c) H. Kato, T. Yoshida, T. Tokue, Y. Nojiri, H. Hirota, T. Ohta, R. M. Williams, S. Tsukamoto, Angew. Chem. 2007, 119, 2304:
30. Angew. Chem. Int. Ed. 2007, 46, 2254;
31. d) A. K. Franz, P. D. Dreyfuss, S. L. Schreiber, J. Am. Chem. Soc. 2007, 129, 1020;
32. e) A. Lerchner, E. M. Carreira, Chem. Eur. J. 2006, 12, 8208.
33. The spiroazetidinone framework is an important structural motif in biologically relevant compounds. See, for example: a) S. Kajii, T. Nishikawa, M. lsobe, Chem. Commun. 2008, 3121;
34. b) A. Macías, A. Morán Ramallal, E. Alonso, C. del Pozo, J. González, J. Org. Chem. 2006, 71, 7721;
35. c) H. Bittermann, F. Bückler, J. Einsiedel, P. Gmeiner, Chem. Eur. J. 2006, 12, 6315;
36. d) P. S. Baran, R. A. Shenvi, J. Am. Chem. Soc. 2006, 128, 14028;
37. e) C. Sun, X. Lin, S. M. Weinreb, J. Org. Chem. 2006, 71, 3159;
38. f) P. S. Baran, R. A. Shenvi, C. A. Mitsos, Angew. Chem. 2005, 117, 3780:
39. Angew. Chem. Int. Ed. 2005, 44, 3714.
40. Bicycles 6 and 7 bear a β-lactam moiety, which, in addition to being the key structural motif in biologically relevant compounds such as antibiotics and enzyme inhibitors, is a versatile building block. For selected reviews, see: a) B. Alcaide, P. Almendros, C. Aragoncillo, Chem. Rev. 2007, 107, 4437;
41. b) Chemistry and Biology of β-Lactam Antibiotics, Vol. 1-3 (Eds.: R. B. Morin, M. Gorman), Academic Press, New York, 1982;
42. c) R. Southgate, C. Branch, S. Coulton, E. Hunt in Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products, Vol. 2 (Ed.: G. Lukacs), Springer, Berlin, 1993, pp.621;
43. d) G. Veinberg, M. Vorona, I. Shestakova, I. Kanepe, E. Lukevics, Curr. Med. Chem. 2003, 10, 1741.
44. NI reactions proceeding via benzylic carbenium ion intermediates, see: a) F. Mühlthau, D. Stadler, A. Goeppert, G. A. Olah, G. K. S. Prakash, T. Bach, J. Am. Chem. Soc. 2006, 128, 9668;
45. b) P. Rubenbauer, T. Bach, Adv. Synth. Catal. 2008, 350, 1125;
46. c) P. Rubenbauer, E. Herdtweck, T. Strassner, T. Bach, Angew. Chem. 2008, 120, 10260:
47. Angew. Chem. Int. Ed. 2008, 47, 10106.