An Expedient Route to (-)-cis-2-Oxabicyclo[3.3.0]oct-6-en-3-one via a meso-Asymmetrization

Synlett

Volumn 1996, Issue 4, 1996, Pages 319-320

  Sugahara, Tsutomu ^a   Ogasawara, Kunio ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001906295     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5437     Document Type: Article

References (16)

1. Sugahara, T.; Ogasawara, K. Tetrahedron Lett. 1996, 37, 205.
2. Takano, S.; Kasahara, C.; Ogasawara, K. Heterocycles 1981, 16, 605.
3. (a) Corey, E. J.; Arnold, Z.; Hulton, J. Tetrahedron Lett. 1970, 307.
4. (b) Partridge, J. J.; Chadha, N. K.; Uskokovic, M. R. J. Am. Chem. Soc. 1973, 95, 7171.
5. Former enantiocontrolled approaches of 13 from meso-precursor: (a) Takano, S.; Tanigawa, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1976, 189. (b) Deardorff, D. R.; Mathhews, A. J.; McMeekin, D. S.; Craney, C. L. Tetrahedron Lett. 1986, 27, 1255 and references cited therein.
6. Former enantiocontrolled approaches of 13 from meso-precursor: (a) Takano, S.; Tanigawa, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1976, 189. (b) Deardorff, D. R.; Mathhews, A. J.; McMeekin, D. S.; Craney, C. L. Tetrahedron Lett. 1986, 27, 1255 and references cited therein.
7. A pertinent monograph: Wong, C. -H; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994.
8. cf. Takano, S.; Higashi, Y.; Kamikubo, T.; Moriya, M.; Ogasawara, K. Synthesis 1993, 948
9. cf. Theil, F.; Weidner, J.; Ballschuh, S.; Kunath, A.; Schick, H. Tetrahedron Lett. 1993, 34, 305.
10. We thank Mr. Shinji Tarama, Toyobo Co., Osaka, Japan, for a donation of lipase LIP
11. Measured with CHIRALCEL OB (eluent: i-PrOH/hexane, 1:9).
12. (a) cf. Ogasawara, K. J. Syn. Org. Chem. Jpn. in press,
13. (b) Tanaka, K.; Ogasawara, K. Synthesis 1995, 1237.
14. cf. Isobe, M.; Ichikawa, Y.; Bai, D. -L.; Goto, T. Tetrahedron 1987, 43, 4767.
15. Mandai, T.; Ueda, M.; Hasegawa, S.; Kawada, M.; Tsuji, J.; Saito, S. Tetrahedron Lett. 1990, 31, 4041.
16. cf. Kamikubo, T.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1995, 1951.