Synthesis of carbocycles by enone-selective reduction using organoiodotin hydride

Tetrahedron Letters

Volumn 41, Issue 18, 2000, Pages 3403-3406

  Suwa, Toshihiro ^a   Nishino, Keita ^a   Miyatake, Masato ^a   Shibata, Ikuya ^a   Baba, Akio ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

1,4 reduction; Enone selective reduction; Intramolecular aldol reaction; Organoiodotin hydride

Indexed keywords

KETONE DERIVATIVE; TIN DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034728936     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00388-9     Document Type: Article

References (16)

1. Heathcock, C. H. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, pp. 133.
2. 2-catalyzed hydrogenation of enone in the presence of ketone: Paquette, L. A.; Kang, H. J. J. Am. Chem. Soc., 1991, 113, 2610.
3. Hutchins, R. O.; Hutchins, M. K. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 8, pp. 25.
4. 2. (a) Sawer, A. K.; Brown, J. E.; Hanson, E. L. J. Organomet. Chem. 1965, 3, 464.
5. 2. (b) Sawer, A. K.; Brown, J. E. J. Organomet. Chem. 1996, 5, 438.
6. Kawakami, T.; Miyatake, M.; Shibata, I.; Baba, A.; Matsuda, H. J. Org. Chem. 1996, 61, 376.
7. 3) δ 3.04 (br, 1H, OH), 3.15 (dd, 1H, J=8.3 and 16.1 Hz, CH), 3.60 (dd, 1H, J=7.8 and 16.1 Hz, CH), 4.31-4.39 (m, 1H, CHCOPh), 5.51 (d, 1H, J=5.8 Hz, CHOH), 7.24-8.05 (m, 9H, Ph).
8. Substrates 1 or 3 were prepared by the reaction of the corresponding dialdehyde with 1 equiv. of a Wittig reagent.
9. 5
10. Moon Kim, B.; Williams, S. F.; Masamune, S. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, pp. 239.
11. (a) Shibata, I.; Yoshida, T.; Baba, A.; Matsuda, H. Chem. Lett. 1991, 307.
12. (b) Kawakami, T.; Shibata, I.; Baba, A. J. Org. Chem. 1996, 61, 82.
13. 2), 7.19-8.02 (m, 9H, Ph).
14. Shibata, I.; Baba, A.; Iwasaki, H.; Matsuda, H. J. Org. Chem. 1986, 51, 2177.
15. The 1,4-reduction of enal was performed in a similar manner by an iodotin hydride complex. Suwa, T.; Shibata, I.; Baba, A. Organometallics 1999, 18, 3965.
16. 3) δ 3.09 (dd, 1H, J=7.3 and 16.1 Hz), 3.25 (dd, 1H, J=7.8 and 16.6 Hz), 3.43 (dd, 1H, J=9.3 and 16.1 Hz), 3.50 (dd, 1H, J=5.9 and 16.6 Hz), 4.09-4.17 (m, 1H), 4.40-4.47 (m, 1H), 7.16-7.98 (m, 14H).