Oxygen Nucleophile Initiated Tandem Conjugate Addition Reactions of 1-Nitro-1-cyclohexene with 4-Hydroxy-2-butynoates: Synthesis of Octahydrobenzo[b]furans

Synlett

Volumn 1996, Issue 10, 1996, Pages 985-986

  Yakura, Takayuki ^a   Tsuda, Tomoko ^a   Matsumura, Yukiko ^a   Yamada, Seiji ^a   Ikeda, Masazumi ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

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Indexed keywords

EID: 0343099456     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5653     Document Type: Article

References (22)

1. Tietze, L. F.; Beifuss, U. Angew. Chem. Int. Ed. Engl. 1993, 32, 131.
2. Ihara, M.; Fukumoto, K. Angew. Chem. Int. Ed. Engl. 1993, 32, 1010.
3. Bunce, R. A. Tetrahedron 1995, 51, 13103.
4. Davies, H. G.; Green, R.H. Nat. Prod. Rep. 1986, 3, 87.
5. Davies, H. G.; Green, R.H. Chem. Soc. Rev. 1991, 20, 211; 271.
6. Peak, S. A.; Smith, A. B., III In Studies in Natural Products Chemistry, Vol. 12; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1993; p 3.
7. The other bases such as triethylamine, 1,8-diazabicyclo[5.4.0]-undec-7-ene, 1,1,3,3-tetramethylguanidine, and basic alumina were ineffective.
8. 3, 300 MHz) δ: 1.5-2.2 (7H, m), 2.9-3.1 (1H, m), 3.69 (3H, s), 4.27 (1H, br s), 4.70 (2H, d, J = 2.2 Hz), 5.84 (1H, t, J = 2.2 Hz).
9. 1. R value of (E)-3a was 0.014 for 1881 reflections and that of (Z)-3a was 0.011 for 1832 reflections. The details will be described elsewhere.
10. Yoshikoshi, A.; Miyashita, M. Acc. Chem. Res. 1985, 18, 284.
11. Barrett, A. G. M.; Graboski, G. G. Chem. Rev. 1986, 86, 751.
12. Ono, N.; Miyake, H.; Kamimura, A.; Hamamoto, I.; Tamura, R.; Kaji, A. Tetrahedron 1985, 41, 4013.
13. Kamimura, A.; Ono, N. Tetrahedron Lett. 1989, 30, 731.
14. Duffy, J. L.; Kurth, J. A.; Kurth, M. J. Tetrahedron Lett. 1993, 34, 1259.
15. Ono, N.; Miyake, H.; Kamimura, A.; Tsukui, N.; Kaji, A. Tetrahedron Lett. 1982, 23, 2957.
16. Ono, N.; Kamimura, A.; Kaji, A. Synthesis 1984, 226.
17. Ono, N.; Miyake, H.; Tamura, R.; Kaji, A. Tetrahedron Lett. 1981, 22, 1705.
18. Compound 5 was isolated as a single diastereoisomer. The stereochemistry of 5 was determined by NOE difference spectroscopy: positive NOE effects were observed between the olefinic proton and H-3a, and H-3a and H-7a.
19. The stereochemistry of the major isomer 6a was assigned on the basis of the assumption that the epoxidation would take place from the convex face of the double bond of 4. Stereoselective oxidation of the related silyl enol ether was reported, see, Fujiwara, S.; Smith, A. B., III Tetrahedron Lett. 1992, 33, 1185.
20. Crandall, J. K.; Lin, L.-H. C. J. Org. Chem. 1968, 33, 2375.
21. 3, 300 MHz) δ: 1.2-2.2 (9H, m), 3.19 (1H, dd, J = 11.7 and 4.1 Hz), 3.74 (3H, s), 4.65 (1H, dd, J = 17.6 and 2.6 Hz), 4.94 (1H, ddd, J = 17.6, 2.6, and 0.8 Hz), 5.85 (1H, t, J = 2.6 Hz).
22. 1H NMR spectra of (E)-3a and 5 is the H-2 proton signal which appears as an AB pattern (further splitting with the olefinic proton was observed) due to the influence of the ester carbonyl group. In contrast the H-2 protons of (Z)-3a have essentially the same chemical shift centered at δ 4.70 (this signal appears as a doublet due to coupling with the olefinic proton). The H-2 protons of 7 exhibited an AB pattern.