Allylic Carbonates. Efficient Allylating Agents of Carbonucleophiles in Palladium-Catalyzed Reactions under Neutral Conditions

Journal of Organic Chemistry

Volumn 50, Issue 9, 1985, Pages 1523-1529

  Tsuji, Jiro ^a   Shimizu, Isao ^a   Minami, Ichiro ^a   Ohashi, Yukihiro ^a   Sugiura, Teruo ^a   Takahashi, Kazuhiko ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845379388     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00209a032     Document Type: Article

References (23)

1. (1) (a) Tsuji, J.; Takahashi, H.; Morikawa, M. Tetrahedron Lett. 1965, 4387–4388. (b) Tsuji, J.; Takahashi, H.; Morikawa, M. Kogyo Kagaku Zasshi 1966, 69, 920–924.
2. (2) Takahashi, K.; Miyake, A.; Hata, G. Bull. Chem. Soc. Jpn. 1972, 45, 230-236; J. Chem. Soc., Chem. Commun. 1970, 1392–1393.
3. (3) Atkins, K. E.; Walker, W. E.; Manyik, R. M. Tetrahedron Lett. 1970, 3821–3824.
4. (4) For reviews, see: (a) Tsuji, J. “Organic Synthesis with Palladium Compounds”; Springer-Verlag: Berlin, 1981. (b) Trost, B. M. Tetrahedron 1977, 33, 2615–2649. (c) Trost, B. M. Acc. Chem. Res. 1980, 13, 385–393.
5. (5) Tanigawa, Y.; Nishimura, K.; Kawasaki, A.; Murahashi, S. Tetrahedron Lett. 1982, 23, 5549–5552.
6. (6) Hirao, T.; Yamada, N.; Ohshiro, Y.; Agawa, T. J. Organomet. Chem. 1982, 236, 409–414.
7. (7) Trost, B. M.; Schmuff, N. R.; Miller, M. J. J. Am. Chem. Soc. 1980, 102, 5979–5981.
8. (8) (a) Tamura, R.; Hegedus, L. S. J. Am. Chem. Soc. 1982, 104, 3727–3729. (b) Ono, N.; Hamamoto, I.; Kato, A. J. Chem. Soc., Chem. Commun. 1982, 821–822.
9. (9) Tsuji, J.; Kataoka, H.; Kobayashi, Y. Tetrahedron Lett. 1981, 22, 2575–2578.
10. (10) (a) Trost, B. M.; Molander, G. A. J. Am. Chem. Soc. 1981, 103, 5969–5972. (b) Trost, B. M.; Warner, R. W. J. Am. Chem. Soc. 1982, 104, 6112-6114; 1983, 105, 5940–5942. (11) Guibe, F.; Saint M'Leux, Y. Tetrahedron Lett. 1981, 22, 3591–3594.
11. (12) As one precedented example of palladium-catalyzed allylation using allylic carbonates, allylation of a malonate anion using a cyclic carbonate has been mentioned. Trost, B. M.; Runge, T. A. J. Am. Chem. Soc. 1981, 103, 7550–7559.
12. (13) Tsuji, J.; Shimizu, I.; Minami, I.; Ohashi, Y. Tetrahedron Lett. 1982, 23, 4809–4812.
13. (14) Fiaud, J. C.; Hibon De Gournay, A.; Larcheveque, M.; Kagan, H. B. J. Organomet. Chem. 1978, 154, 175–185. (15) Trost, B. M.; Lautens, M. J. Am. Chem. Soc. 1982, 104, 5543-5545; 1983, 105, 3343–3344. A similar nucleophilic reaction using allylic carbonate or acetate catalyzed by tungsten compounds has been reported. Trost, B. M.; Hung, M. H. J. Am. Chem. Soc. 1983, 105, 7757–7759.
14. (17) Tsuji, J.; Ueno, H.; Kobayashi, Y.; Okumoto, H. Tetrahedron Lett. 1981, 22, 2573–2574.
15. (18) Wade, P. A.; Morrow, S. D.; Hardinger, S. A. J. Org. Chem. 1982, 47, 365–367. (19) A stoichiometric nucleophilic reaction of allylic sulfones with (π-allyl)palladium complexes has been reported. Manchand, P. S.; Wong, H. S.; Blount, J. F. J. Org. Chem. 1978, 43, 4769–4774.
16. (20) Rhoads, S. J.; Raulins, N. R. Org. React. (N.Y.) 1975, 22, 1–252. (21) Trost, B. M.; Weber, L.; Strege, P. E.; Fullerton, T. J.; Dietsche, T. J. J. Am. Chem. Soc. 1978, 100, 3416–3426.
17. (22) See: Jeffrey, P. D.; McCombie, S. W. J. Org. Chem. 1982, 47, 587–590, footnote 4.
18. (23) Tsuji, J.; Yamakawa, T.; Kaito, M.; Mandai, T. Tetrahedron Lett. 1978, 2075–2078.
19. (24) Trost, B. M.; Verhoeven, T. R.; Fortunak, J. M. Tetrahedron Lett. 1979, 2301–2304. (25) Tsuji, J.; Sato, K.; Okumoto, H. Tetrahedron Lett. 1982, 23, 5189-5190; J. Org. Chem. 1984, 49, 1341–1344.
20. (26) Tsuji, J.; Minami, I.; Shimizu, I. Tetrahedron Lett. 1983, 24, 1793-1796.
21. (27) Tsuji, J.; Minami, I.; Shimizu, I. Chem. Lett. 1983, 1325–1326.
22. (28) Tsuji, J.; Takahashi, K.; Minami, I.; Shimizu, I. Tetrahedron Lett. 1984, 25, 4783–4786. (29) Ukai, T.; Kawazura, H.; Ishii, Y.; Bonnet, J. J.; Ibers, J. A. J. Organomet. Chem. 1974, 65, 253–266.
23. (32) Crombie, L.; Hemesley, P.; Pattenden, G. J. Chem. Soc. 1969, 1016–1024.