Lactone synthesis based on atom transfer carbonylation

Organic Letters

Volumn 2, Issue 3, 2000, Pages 389-391

  Kreimerman, Sergio ^a   Ryu, Ilhyong ^a   Minakata, Satoshi ^a   Komatsu, Mitsuo ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000487372     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9913441     Document Type: Article

References (24)

1. (a) Colquhoun, H. M.; Thompson, D. J.; Twigg, M. V. Carbonylation: Direct Synthesis of Carbonyl Compounds; Plenum: New York, 1991. For reviews on radical carbonylation, see:
2. (b) Ryu, I.; Sonoda, N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1050.
3. Ryu, I.; Sonoda N.; Curran D. P. Chem. Rev. 1996, 96, 177.
4. Chatgilialoglu, C.; Crich, D.; Komatsu, M.; Ryu, I. Chem. Rev. 1999, 99, 1991.
5. For examples of transition metal-catalyzed carbonylation of vinyl and aryl halo alcohols leading to lactones, see. (a) Aoyagi, S.; Hasegawa, Y.; Hirashima S.; Kibayashi, C. Tetrahedron Lett. 1998, 39, 2149.
6. (b) Luo, F.-T.; Wang, M.-W.; Liu, Y.-S. Heterocycles 1996, 43, 2725.
7. (c) Suzuki, T.; Uozumi, Y.; Shibasaki, M. J. Chem. Soc., Chem. Commun. 1991, 1593.
8. (d) Martin, L. D.; Stille, J. K. J. Org. Chem. 1982, 47, 3630.
9. (e) Cowell, A.; Stille, J. K. J. Am. Chem. Soc. 1980, 102, 4193.
10. (f) Mori, M.; Chiba, K.; Inotsume, N.; Ban, Y. Heterocycles 1979, 12, 921.
11. For recent examples of transition metal-catalyzed carbonylation of unsaturated alcohols leading to lactones, see: (a) Cao, P.; Zhang, X. J. Am. Chem. Soc. 1999, 121, 7708.
12. (b) Ogawa, A.; Kawabe, K.; Kawakami, J.; Mihara, M.; Hirao, T. Organometallics 1998, 17, 3111.
13. (c) Brunner, M.; Alper, H. J. Org. Chem. 1997, 62, 7565.
14. (d) Ukaji, Y.; Miyamoto, M.; Mikuni, M.; Takeuchi, S.; Inomata, K. Bull. Chem. Soc. Jpn. 1996, 69, 735.
15. For lactone synthesis by the Pd-catalyzed carbonylation of perfluorinated alkyl iodides, see: Urata, H.; Yugari, H.; Fuchikami, T. Chem. Lett. 1987, 836.
16. We have recently developed a new route for the synthesis of δ-lactones by oxidative radical carbonylation of saturated alcohols, see: (a) Tsunoi, S.; Ryu, I.; Okuda, T.; Tanaka, M.; Komatsu M.; Sonoda, N. J. Am. Chem. Soc. 1998, 120, 8962.
17. (b) Tsunoi, S.; Ryu. I.; Sonoda, N. J. Am. Chem. Soc. 1994, 116, 5473.
18. (a) Nagahara, K.; Ryu, I.; Komatsu, M.; Sonoda, N. J. Am. Chem. Soc. 1997, 119, 5465.
19. (b) Ryu, I. Nagahara, K.; Kambe, N.; Sonoda. N.; Kreimerman, S.; Komatsu, M. Chem. Commun. 1998, 1953.
20. A hybrid radical/ionic system is also useful for atom transfer reactions other than carbonylation, see: (a) Joung, M. J.; Ahn, J. H.; Lee, D. W.; Yoon, N. M. J. Org. Chem. 1998, 63, 2755.
21. (b) Curran, D. P.; Ko, S.-B. Tetrahedron Lett. 1998, 39, 6629.
22. 4. 1c and 1f were prepared by the reaction of 2-ethyl-1,3-hexanediol and 1,3-butanediol, respectively, with diiodosilane, see: Keinan, E.; Perez, D. J. Org. Chem. 1987, 52, 4846. 1d was prepared from the same precursor as 1c by using a standard MsCl/NaI reaction.
23. 4. 1c and 1f were prepared by the reaction of 2-ethyl-1,3-hexanediol and 1,3-butanediol, respectively, with diiodosilane, see: Keinan, E.; Perez, D. J. Org. Chem. 1987, 52, 4846. 1d was prepared from the same precursor as 1c by using a standard MsCl/NaI reaction.
24. For a similar reaction with the use of a Pd catalyst, see ref 4.