Extremely facile and selective nickel-catalyzed allyl ether cleavage

Angewandte Chemie - International Edition

Volumn 37, Issue 8, 1998, Pages 1136-1137

  Taniguchi, Takahiko ^a   Ogasawara, Kunio ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Allyl ethers; Aluminum; Cleavage reactions; Nickel; Protecting groups

Indexed keywords

EID: 0032482051     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980504)37:8<1136::AID-ANIE1136>3.0.CO;2-Z     Document Type: Article

References (16)

1. For a pertinent review, see: F. Guibe, Tetrahedron, 1997, 53, 13509-13556.
2. For pertinent monographs, see: a) T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, 2nd ed., Wiley, New York, 1991; b) P. J. Kocienski, Protective Groups, Thieme, Stuttgart, 1994.
3. For pertinent monographs, see: a) T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, 2nd ed., Wiley, New York, 1991; b) P. J. Kocienski, Protective Groups, Thieme, Stuttgart, 1994.
4. H. M. Colquhoun, J. Holton, D. J. Thompson, M. V. Twigg, New Pathways for Organic Synthesis, Plenum, New York, 1988.
5. K. Fischer, K. Jonas, P. Misbach, R. Stabba, G. Wilke, Angew. Chem. 1973, 85, 1002-1012; Angew. Chem. Int. Ed. Engl. 1973, 12, 943-1026.
6. K. Fischer, K. Jonas, P. Misbach, R. Stabba, G. Wilke, Angew. Chem. 1973, 85, 1002-1012; Angew. Chem. Int. Ed. Engl. 1973, 12, 943-1026.
7. A nickel-catalyzed reductive cleavage of cyclic allyl ethers with DIBAL has been reported recently, see: M. Lautens, P. Chin, S. Ma, T. Rovis, J. Am. Chem. Soc. 1995, 117, 532-533.
8. 4 (60 MHz): δ = 5.73 (m, 1H), 4.97 (m, 1H), 4.88 (m, 1H), 1.72 (dt, 3H). See: A. A. Bothner-By, C. Naar-Colin, J. Am. Chem. Soc. 1961, 83, 231-236.
9. J. Eisch in Comprehensive Organic Synthesis, Vol. 8 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, pp. 733-761.
10. For a pertinent review, see: E. Winterfeldt, Synthesis 1975, 617-630.
11. For examples reported by our group, see: a) S. Takano, M. Akiyama, S. Sato, K. Ogasawara, Chem. Lett. 1983, 1593-1596; b) S. Takano, M. Akiyama, K. Ogasawara, Heterocycles 1983, 20, 2237-2238; S. Takano, M. Akiyama, K. Ogasawara, Chem. Pharm. Bull. 1984, 32, 791-794; S. Takano, A. Kurotaki, Y. Sekiguchi, S. Satoh, M. Hirama, K. Ogasawara, Synthesis 1986, 811-817;
12. For examples reported by our group, see: a) S. Takano, M. Akiyama, S. Sato, K. Ogasawara, Chem. Lett. 1983, 1593-1596; b) S. Takano, M. Akiyama, K. Ogasawara, Heterocycles 1983, 20, 2237-2238; S. Takano, M. Akiyama, K. Ogasawara, Chem. Pharm. Bull. 1984, 32, 791-794; S. Takano, A. Kurotaki, Y. Sekiguchi, S. Satoh, M. Hirama, K. Ogasawara, Synthesis 1986, 811-817;
13. For examples reported by our group, see: a) S. Takano, M. Akiyama, S. Sato, K. Ogasawara, Chem. Lett. 1983, 1593-1596; b) S. Takano, M. Akiyama, K. Ogasawara, Heterocycles 1983, 20, 2237-2238; S. Takano, M. Akiyama, K. Ogasawara, Chem. Pharm. Bull. 1984, 32, 791-794; S. Takano, A. Kurotaki, Y. Sekiguchi, S. Satoh, M. Hirama, K. Ogasawara, Synthesis 1986, 811-817;
14. For examples reported by our group, see: a) S. Takano, M. Akiyama, S. Sato, K. Ogasawara, Chem. Lett. 1983, 1593-1596; b) S. Takano, M. Akiyama, K. Ogasawara, Heterocycles 1983, 20, 2237-2238; S. Takano, M. Akiyama, K. Ogasawara, Chem. Pharm. Bull. 1984, 32, 791-794; S. Takano, A. Kurotaki, Y. Sekiguchi, S. Satoh, M. Hirama, K. Ogasawara, Synthesis 1986, 811-817;
15. e) S. Takano, S. Satoh, K. Ogasawara, J. Chem. Soc. Chem. Commun. 1988, 59-60.
16. 2(dppp)] in toluene loses its activity within a week on standing at - 20°C.