Palladium-catalyzed arylation of α-allenic alcohols with hypervalent iodonium salts: Synthesis of epoxides and diol cyclic carbonates

Tetrahedron Letters

Volumn 39, Issue 15, 1998, Pages 2127-2130

  Kang, Suk Ku ^a   Yamaguchi, Tokutaro ^a   Pyun, Sung Jae ^a   Lee, Yong Tack ^a   Baik, Tae Gon ^a  

^a Sungkyunkwan University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALLENE DERIVATIVE; CARBONIC ACID; EPOXIDE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; SYNTHESIS;

EID: 0032499085     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00076-8     Document Type: Article

References (20)

1. 1. (a) Djahanbuni, D.; Cazes, B.; Gore, J. Tetrahedron Lett. 1984, 25, 203-206.
2. (b) Nokami, J.; Maihara, A.; Tsuji, J. Tetrahedron Lett. 1990, 31, 5629-5630.
3. (c) Larock, R. C.; Berrios-Pena, N.G.; Fried, C. A. J. Org. Chem. 1991, 56, 2615-2617.
4. (d) Yamamoto, Y.; Al-Masum, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 6019-6020.
5. 2. Cazes, B. Pure Appl. Chem. 1990, 62, 1867-1878.
6. 3. Shimizu, I.; Sugiura, T.; Tsuji, J. J. Org. Chem. 1985, 50, 537-539.
7. 4. For recent reviews: (a) Stang, P. J. Angew. Chem. Int. Ed. Engl. 1992, 31, 274-285.
8. (b) Moriarty, R. M.; Viad, R. K. Synthesis 1990, 431-447.
9. (c) Ochiai, M. Rev. Heteroatm. Chem. 1989, 2, 92-111.
10. 5. (a) Kang, S-K.; Lee, H-W.; Kim, J-S.; Choi, S-C. Tetrahedron Lett. 1996, 37, 3723-3726.
11. (b) Kang, S-K.; Lee, H-W.; Jang, S-B.; Ho, P-S. J. Org. Chem. 1996, 61, 4720-4724.
12. (c) Kang, S-K.; Lee, H-W.; Jang, S-B.; Ho, P-S. J. Chem. Soc. Chem. Commun. 1996, 835-836.
13. (d) Kang, S-K.; Jung, K-Y.; Park, C-H.; Jang, S-B. Tetrahedron Lett. 1995, 36, 8047-8050.
14. (e) Kang, S-K.; Lee, H-W.; Jang, S-B.; Kim, T-H.; Pyun, S-J. J. Org. Chem. 1996, 61, 2604-2605.
15. 6. The α-allenic alcohols were converted to syn-diol via iodocyclization: Friesen, R.W.; Giroux, A. Tetrahedron Lett. 1993, 34, 1867-1870.
16. 7. Crabbe, P.; Nassim, B.; Rovert-Lopes, M. T. Org. Synth. 1984, 63, 203-205.
17. 3, 75 MHz) δ 13.81, 22.27, 24.05, 31.09, 33.92, 81.55, 82.41, 116.70, 127.20, 128.70, 128.87, 136.90, 143.84, 154.37.
18. f = 0.55) to afford the trans-epoxide 3a (93.7 mg, 62%).
19. 3CN, the major product was ketone instead of trans-epoxide.
20. 11. Generous financial support from KOSEF (97-0501-02-01-3) and Ministry of Education (BSRI-97-3420) is gratefully acknowledged.