A New Route to γ-Ketoaldehydes. Application to the Synthesis of cis-Jasmone

Journal of the American Chemical Society

Volumn 95, Issue 13, 1973, Pages 4446-4447

  Oshima, Koichiro ^a   Yamamoto, Hisashi ^a   Nozaki, Hitosi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33947087636     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00794a064     Document Type: Letter

References (17)

1. K. Oshima, H. Takahashi, H. Yamamoto, and H. Nozaki, J. Amer. Chem. Soc, 95, 2693 (1973).
2. Recently a variety of new synthetic methods for the preparation of 1, 4-diketone has been developed; see (a) G. Stork and R. Borch, J. Amer. Chem. Soc, 86, 935 (1964);
3. G. Biichi and H. Wüest, J. Org. Chem., 31, 977 (1966);
4. E. J. Corey and L. S. Hegedus, J. Amer. Chem. Soc, 91, 4926 (1969);
5. E. Wenkert, R. A. Mueller, E. J. Reardon, Jr., S. S. Sathe, D. J. Scharf, and G. Tosi, J. Amer. Chem. Soc, 92, 7428 (1970);
6. J. E. Mc-Murry and J. Melton, J. Amer. Chem. Soc, 93, 5309 (1971);
7. T. Mukaiyama, K. Narasaka, and M. Furusato, J. Amer. Chem. Soc, 94, 8641 (1972).
8. This sulfide was prepared by the sequence 2-ethoxy-2-propen-l-ol [W. Grell and H. Mchleidt, Justus Liebigs Ann. Chem., 699, 53 (1966)] — 3-bromo-2-ethoxypropene (n-butyllithium-methanesulfonyl chloride-lithium bromide in ether:
9. E. J. Corey, H. Yamamoto, D. K. Herron, and K. Achiwa, J. Amer. Chem. Soc., 92, 6635 (1970)) — 2-ethoxyallyl vinyl sulfide (lithium ethenethiolate in liquid ammonia:
10. L. Brandsma, P. J. W. Schuijl, Reel. Trav. Chim. Pays-Bas, 88, 513 (1969)) (30% over-all yield after distillation). Nmr (CCh, TMS) 5 1. 30 (t, 3 H, / = 7. 5 Hz), 3. 23 (s, 2 H), 3. 25 (q, 2 H, / = 7. 5 Hz), 3. 94 and 4. 08 (2 d, 1 H each, J = 2 Hz), 5. 08 (d, 1 H, J = 16 Hz), 5. 13 (d, 1 H, J = 9 Hz), 6. 32 (dd, 1H, J= 9 and 16 Hz).
11. Recently the Claisen rearrangement of 2-ethoxyallyl ester was reported: R. E. Ireland and R. H. Mueller, J. Amer. Chem. Soc, 94, 5897 (1972).
12. G. Büchi and B. Egger, J. Org. Chem., 36, 2021 (1971);
13. P. A. Grieco, J. Org. Chem., 37, 2363 (1972).
14. H. C. Ho, T. -L. Ho, and C. M. Wong, Can. J. Chem., 50, 2718 (1972).
15. H. Hunsdiecker, Chem. Ber., 75, 455, 447 (1942).
16. L. Crombie, A. J. B. Edgar, S. H. Harper, M. W. Lowe, and D. Thompson, J. Chem. Soc., 3552 (1950)
17. T. Mukaiyama, S. Kobayashi, K. Kamio, and H. Takel, Chem.Lett., 237 (1972).