Palladium-catalyzed stereospecific ring expansion reaction of allenylcyclobutanols with aryl iodides: A novel route to the α-substituted cyclopentanones with quaternary carbon stereocenters

Tetrahedron Letters

Volumn 41, Issue 26, 2000, Pages 5089-5092

  Yoshida, Masahiro ^a   Sugimoto, Kenji ^a   Ihara, Masataka ^a  

^a Lab of Molec and Biochem Toxicol Grad Sch Pharmaceutical Sci T   (Japan)

Author keywords

Cyclopentanones; Palladium and compounds; Rearrangements; Ring transformations

Indexed keywords

ALLENE DERIVATIVE; ALLENYLCYCLOBUTANOL; CYCLOPENTANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMERISM; STEREOISOMERISM; STEREOSPECIFICITY; SYNTHESIS;

EID: 0034709577     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00779-6     Document Type: Article

References (15)

1. For some recent works on the palladium-catalyzed ring expansion of cyclobutanols, see: (a) Mitchell, D.; Liebeskind, L. S. J. Am. Chem. Soc. 1990, 112, 291-296. (b) de Almeida Barbosa, L.-C.; Mann, J. J. Chem. Soc., Perkin Trans. 1 1990, 177. (c) Kim, S.; Uh, K. H.; Lee, S.; Park, J. H. Tetrahedron Lett. 1990, 32, 3395-3396. (d) Nemoto, H.; Nagamochi, M.; Fukumoto, K. J. Org. Chem. 1994, 59, 74-79. (e) Nemoto, H.; Miyata, J.; Yoshida, M.; Raku, N.; Fukumoto, K. J. Org. Chem. 1997, 62, 7850-7857. (f) Nemoto, H.; Yoshida, M.; Fukumoto, K.; Ihara, M. Tetrahedron Lett. 1999, 40, 907-910. (g) Nemoto, H.; Miyata, J.; Ihara, M. Tetrahedron Lett. 1999, 40, 1933-1936. (h) Nemoto, H.; Takahashi, E.; Ihara, M. Org. Lett. 1999, 1, 517-519. (i) Yoshida, M.; Nemoto, H.; Ihara, M. Tetrahedron Lett. 1999, 40, 8583-8586.
2. For some recent works on the palladium-catalyzed ring expansion of cyclobutanols, see: (a) Mitchell, D.; Liebeskind, L. S. J. Am. Chem. Soc. 1990, 112, 291-296. (b) de Almeida Barbosa, L.-C.; Mann, J. J. Chem. Soc., Perkin Trans. 1 1990, 177. (c) Kim, S.; Uh, K. H.; Lee, S.; Park, J. H. Tetrahedron Lett. 1990, 32, 3395-3396. (d) Nemoto, H.; Nagamochi, M.; Fukumoto, K. J. Org. Chem. 1994, 59, 74-79. (e) Nemoto, H.; Miyata, J.; Yoshida, M.; Raku, N.; Fukumoto, K. J. Org. Chem. 1997, 62, 7850-7857. (f) Nemoto, H.; Yoshida, M.; Fukumoto, K.; Ihara, M. Tetrahedron Lett. 1999, 40, 907-910. (g) Nemoto, H.; Miyata, J.; Ihara, M. Tetrahedron Lett. 1999, 40, 1933-1936. (h) Nemoto, H.; Takahashi, E.; Ihara, M. Org. Lett. 1999, 1, 517-519. (i) Yoshida, M.; Nemoto, H.; Ihara, M. Tetrahedron Lett. 1999, 40, 8583-8586.
3. For some recent works on the palladium-catalyzed ring expansion of cyclobutanols, see: (a) Mitchell, D.; Liebeskind, L. S. J. Am. Chem. Soc. 1990, 112, 291-296. (b) de Almeida Barbosa, L.-C.; Mann, J. J. Chem. Soc., Perkin Trans. 1 1990, 177. (c) Kim, S.; Uh, K. H.; Lee, S.; Park, J. H. Tetrahedron Lett. 1990, 32, 3395-3396. (d) Nemoto, H.; Nagamochi, M.; Fukumoto, K. J. Org. Chem. 1994, 59, 74-79. (e) Nemoto, H.; Miyata, J.; Yoshida, M.; Raku, N.; Fukumoto, K. J. Org. Chem. 1997, 62, 7850-7857. (f) Nemoto, H.; Yoshida, M.; Fukumoto, K.; Ihara, M. Tetrahedron Lett. 1999, 40, 907-910. (g) Nemoto, H.; Miyata, J.; Ihara, M. Tetrahedron Lett. 1999, 40, 1933-1936. (h) Nemoto, H.; Takahashi, E.; Ihara, M. Org. Lett. 1999, 1, 517-519. (i) Yoshida, M.; Nemoto, H.; Ihara, M. Tetrahedron Lett. 1999, 40, 8583-8586.
4. For some recent works on the palladium-catalyzed ring expansion of cyclobutanols, see: (a) Mitchell, D.; Liebeskind, L. S. J. Am. Chem. Soc. 1990, 112, 291-296. (b) de Almeida Barbosa, L.-C.; Mann, J. J. Chem. Soc., Perkin Trans. 1 1990, 177. (c) Kim, S.; Uh, K. H.; Lee, S.; Park, J. H. Tetrahedron Lett. 1990, 32, 3395-3396. (d) Nemoto, H.; Nagamochi, M.; Fukumoto, K. J. Org. Chem. 1994, 59, 74-79. (e) Nemoto, H.; Miyata, J.; Yoshida, M.; Raku, N.; Fukumoto, K. J. Org. Chem. 1997, 62, 7850-7857. (f) Nemoto, H.; Yoshida, M.; Fukumoto, K.; Ihara, M. Tetrahedron Lett. 1999, 40, 907-910. (g) Nemoto, H.; Miyata, J.; Ihara, M. Tetrahedron Lett. 1999, 40, 1933-1936. (h) Nemoto, H.; Takahashi, E.; Ihara, M. Org. Lett. 1999, 1, 517-519. (i) Yoshida, M.; Nemoto, H.; Ihara, M. Tetrahedron Lett. 1999, 40, 8583-8586.
5. For some recent works on the palladium-catalyzed ring expansion of cyclobutanols, see: (a) Mitchell, D.; Liebeskind, L. S. J. Am. Chem. Soc. 1990, 112, 291-296. (b) de Almeida Barbosa, L.-C.; Mann, J. J. Chem. Soc., Perkin Trans. 1 1990, 177. (c) Kim, S.; Uh, K. H.; Lee, S.; Park, J. H. Tetrahedron Lett. 1990, 32, 3395-3396. (d) Nemoto, H.; Nagamochi, M.; Fukumoto, K. J. Org. Chem. 1994, 59, 74-79. (e) Nemoto, H.; Miyata, J.; Yoshida, M.; Raku, N.; Fukumoto, K. J. Org. Chem. 1997, 62, 7850-7857. (f) Nemoto, H.; Yoshida, M.; Fukumoto, K.; Ihara, M. Tetrahedron Lett. 1999, 40, 907-910. (g) Nemoto, H.; Miyata, J.; Ihara, M. Tetrahedron Lett. 1999, 40, 1933-1936. (h) Nemoto, H.; Takahashi, E.; Ihara, M. Org. Lett. 1999, 1, 517-519. (i) Yoshida, M.; Nemoto, H.; Ihara, M. Tetrahedron Lett. 1999, 40, 8583-8586.
6. For some recent works on the palladium-catalyzed ring expansion of cyclobutanols, see: (a) Mitchell, D.; Liebeskind, L. S. J. Am. Chem. Soc. 1990, 112, 291-296. (b) de Almeida Barbosa, L.-C.; Mann, J. J. Chem. Soc., Perkin Trans. 1 1990, 177. (c) Kim, S.; Uh, K. H.; Lee, S.; Park, J. H. Tetrahedron Lett. 1990, 32, 3395-3396. (d) Nemoto, H.; Nagamochi, M.; Fukumoto, K. J. Org. Chem. 1994, 59, 74-79. (e) Nemoto, H.; Miyata, J.; Yoshida, M.; Raku, N.; Fukumoto, K. J. Org. Chem. 1997, 62, 7850-7857. (f) Nemoto, H.; Yoshida, M.; Fukumoto, K.; Ihara, M. Tetrahedron Lett. 1999, 40, 907-910. (g) Nemoto, H.; Miyata, J.; Ihara, M. Tetrahedron Lett. 1999, 40, 1933-1936. (h) Nemoto, H.; Takahashi, E.; Ihara, M. Org. Lett. 1999, 1, 517-519. (i) Yoshida, M.; Nemoto, H.; Ihara, M. Tetrahedron Lett. 1999, 40, 8583-8586.
7. For some recent works on the palladium-catalyzed ring expansion of cyclobutanols, see: (a) Mitchell, D.; Liebeskind, L. S. J. Am. Chem. Soc. 1990, 112, 291-296. (b) de Almeida Barbosa, L.-C.; Mann, J. J. Chem. Soc., Perkin Trans. 1 1990, 177. (c) Kim, S.; Uh, K. H.; Lee, S.; Park, J. H. Tetrahedron Lett. 1990, 32, 3395-3396. (d) Nemoto, H.; Nagamochi, M.; Fukumoto, K. J. Org. Chem. 1994, 59, 74-79. (e) Nemoto, H.; Miyata, J.; Yoshida, M.; Raku, N.; Fukumoto, K. J. Org. Chem. 1997, 62, 7850-7857. (f) Nemoto, H.; Yoshida, M.; Fukumoto, K.; Ihara, M. Tetrahedron Lett. 1999, 40, 907-910. (g) Nemoto, H.; Miyata, J.; Ihara, M. Tetrahedron Lett. 1999, 40, 1933-1936. (h) Nemoto, H.; Takahashi, E.; Ihara, M. Org. Lett. 1999, 1, 517-519. (i) Yoshida, M.; Nemoto, H.; Ihara, M. Tetrahedron Lett. 1999, 40, 8583-8586.
8. For some recent works on the palladium-catalyzed ring expansion of cyclobutanols, see: (a) Mitchell, D.; Liebeskind, L. S. J. Am. Chem. Soc. 1990, 112, 291-296. (b) de Almeida Barbosa, L.-C.; Mann, J. J. Chem. Soc., Perkin Trans. 1 1990, 177. (c) Kim, S.; Uh, K. H.; Lee, S.; Park, J. H. Tetrahedron Lett. 1990, 32, 3395-3396. (d) Nemoto, H.; Nagamochi, M.; Fukumoto, K. J. Org. Chem. 1994, 59, 74-79. (e) Nemoto, H.; Miyata, J.; Yoshida, M.; Raku, N.; Fukumoto, K. J. Org. Chem. 1997, 62, 7850-7857. (f) Nemoto, H.; Yoshida, M.; Fukumoto, K.; Ihara, M. Tetrahedron Lett. 1999, 40, 907-910. (g) Nemoto, H.; Miyata, J.; Ihara, M. Tetrahedron Lett. 1999, 40, 1933-1936. (h) Nemoto, H.; Takahashi, E.; Ihara, M. Org. Lett. 1999, 1, 517-519. (i) Yoshida, M.; Nemoto, H.; Ihara, M. Tetrahedron Lett. 1999, 40, 8583-8586.
9. For some recent works on the palladium-catalyzed ring expansion of cyclobutanols, see: (a) Mitchell, D.; Liebeskind, L. S. J. Am. Chem. Soc. 1990, 112, 291-296. (b) de Almeida Barbosa, L.-C.; Mann, J. J. Chem. Soc., Perkin Trans. 1 1990, 177. (c) Kim, S.; Uh, K. H.; Lee, S.; Park, J. H. Tetrahedron Lett. 1990, 32, 3395-3396. (d) Nemoto, H.; Nagamochi, M.; Fukumoto, K. J. Org. Chem. 1994, 59, 74-79. (e) Nemoto, H.; Miyata, J.; Yoshida, M.; Raku, N.; Fukumoto, K. J. Org. Chem. 1997, 62, 7850-7857. (f) Nemoto, H.; Yoshida, M.; Fukumoto, K.; Ihara, M. Tetrahedron Lett. 1999, 40, 907-910. (g) Nemoto, H.; Miyata, J.; Ihara, M. Tetrahedron Lett. 1999, 40, 1933-1936. (h) Nemoto, H.; Takahashi, E.; Ihara, M. Org. Lett. 1999, 1, 517-519. (i) Yoshida, M.; Nemoto, H.; Ihara, M. Tetrahedron Lett. 1999, 40, 8583-8586.
10. Nemoto, H.; Yoshida, M.; Fukumoto, K. J. Org. Chem. 1997, 62, 6450-6451.
11. Recently, Nagao et al. reported the palladium-catalyzed hetero- and carbocyclic ring expansion reactions of allenic alcohols having a substituent at the 1-position of the allenyl moiety. (a) Jeong, I.-Y.; Nagao, Y. Tetrahedron Lett. 1998, 39, 8677-8680. (b) Jeong, I.-Y.; Nagao, Y. Synlett 1999, 576-578.
12. Recently, Nagao et al. reported the palladium-catalyzed hetero- and carbocyclic ring expansion reactions of allenic alcohols having a substituent at the 1-position of the allenyl moiety. (a) Jeong, I.-Y.; Nagao, Y. Tetrahedron Lett. 1998, 39, 8677-8680. (b) Jeong, I.-Y.; Nagao, Y. Synlett 1999, 576-578.
13. 1H NOESY.
14. 20O: C, 86.92; H, 7.29. Found: C, 86.53; H, 7.16.
15. As an alternative pathway, it is also possible that the chelation of the hydroxyl group to the cationic palladium species would cause the formation of conformer A.