High pressure mediated asymmetric diels-alder reaction of chiral sulfinylacrylate derivatives with furan and 2-methoxyfuran

Heterocycles

Volumn 42, Issue 1, 1996, Pages 129-133

  Yamakoshi, Yoko Nakajima ^a,b,c   Ge, Wei Ying ^a   Sugita, Jun ^a   Okayama, Kazuya ^a   Takahashi, Tamiko ^a   Koizumi, Toru ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

^b Sci and Technology Agency of Japan   (Japan)

^c Natl Institute of Health Sciences

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000687759     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-95-s43     Document Type: Article

References (16)

1. E. J. Corey and T.-P. Loh, Tetrahedron Lett., 1993, 34, 3979, and references cited therein.
2. (a) E. Vieira and P. Vogel, Helv. Chim. Acta, 1983, 66, 1865;
3. (b) H. Takayama, A. Iyobe, and T. Koizumi, J. Chem. Soc., Chem. Commun., 1986, 771;
4. (c) H. Takayama, K. Hayashi, and T. Koizumi, Tetrahedron Lett., 1986, 27, 5509;
5. (d) T. Takahashi, T. Namiki, Y. Takeuchi, and T. Koizumi, Chem. Pharm. Bull., 1988, 36, 3215;
6. (e) Y. Arai, M. Matsui, T. Koizumi, and M. Shiro, J. Org. Chem., 1991, 56, 1983;
7. (f) I. Ikeda, A. Gondo, M. Shiro, and K. Kanematsu, Heterocycles, 1993, 36, 2669.
8. Asymmetric D-A reaction of di-l-menthyl acetoxymethylenemalonate with furan gave endo (40% yield, 54% de) and exo cycloadducts (20% yield, 61% de) under high pressure conditions: N. Katagiri, H. Akatsuka, C. Kaneko, and A. Sera, Tetrahedron Lett., 1988, 29, 5397.
9. (a) Y. Arai, M. Matsui, and T. Koizumi, Synthesis, 1990, 320;
10. (b) Y. Arai and T. Koizumi, Sulfur Reports, 1993, 15, 41.
11. O. De Lucchi, V. Lucchini, C. Marchioro, G. Valle, and G. Modena, J. Org. Chem., 1986, 51, 1457.
12. 1H nmr, mass) data were obtained for all new isolable compounds.
13. 8 and oxidation with m-chloroperbenzoic acid in 43% overall yield.
14. M. E. Jung and K. R. Buszek, J. Am. Chem. Soc., 1988, 110, 3965.
15. w = 4.4%. The authors have deposited atomic coordinates for 6b with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
16. T. Takeuchi, H. Chimura, M. Hamada, H. Umezawa, O. Yoshioka, N. Oguchi, Y. Takahashi, and A. Matsuda, J. Antibiot., 1975, 28, 737.