Catalytic kinetic resolution reaction of (±)-5- methylbicyclo[3.3.0]oct-1-ene-3,6-dione

Journal of Organic Chemistry

Volumn 64, Issue 14, 1999, Pages 5318-5320

  Emori, Eita ^a   Iida, Takehiko ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

5 METHYLBICYCLO[3.3.0]OCT 1 ENE 3,6 DIONE; CARBONYL DERIVATIVE; THIOPHENOL; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; RACEMIC MIXTURE; STEREOISOMERISM; SYNTHESIS;

EID: 0033067092     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9904922     Document Type: Article

References (16)

1. Emori, E.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 4043-4044.
2. Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1236-1256.
3. For other catalytic asymmetric Michael additions of thiols, see: (a) Suzuki, K.; Ikegawa, A.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1982, 55, 3277-3282. (b) Nishimura, K; Ono, M.; Nagaoka, Y.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 12974-12975. (c) Tomioka, K.; Okuda, M.; Nishimura, K.; Manabe, S.; Kanai, M.; Nagaoka, Y.; Koga, K. Tetrahedron Lett. 1998, 39, 2141-2144.
4. For other catalytic asymmetric Michael additions of thiols, see: (a) Suzuki, K.; Ikegawa, A.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1982, 55, 3277-3282. (b) Nishimura, K; Ono, M.; Nagaoka, Y.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 12974-12975. (c) Tomioka, K.; Okuda, M.; Nishimura, K.; Manabe, S.; Kanai, M.; Nagaoka, Y.; Koga, K. Tetrahedron Lett. 1998, 39, 2141-2144.
5. For other catalytic asymmetric Michael additions of thiols, see: (a) Suzuki, K.; Ikegawa, A.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1982, 55, 3277-3282. (b) Nishimura, K; Ono, M.; Nagaoka, Y.; Tomioka, K. J. Am. Chem. Soc. 1997, 119, 12974-12975. (c) Tomioka, K.; Okuda, M.; Nishimura, K.; Manabe, S.; Kanai, M.; Nagaoka, Y.; Koga, K. Tetrahedron Lett. 1998, 39, 2141-2144.
6. Trost, B. M.; Curran, D. P. J. Am. Chem. Soc. 1980, 102, 5699-5700.
7. Trost, B. M.; Curran, D. P. J. Am. Chem. Soc. 1981, 103, 7380-7381.
8. Trost, B. M.; Curran, D. P. Tetrahedron Lett. 1981, 22, 4929-4932.
9. Brooks, D. W.; Woods, K. W. J. Org. Chem. 1987, 52, 2036-2039.
10. The reaction at 0 °C gave 2′ in 62% ee.
11. 13C NMR spectrum.
12. The addition of 18 mol % of (R)-BINOL gave similar results.
13. For the effects of tert-butyl alcohol on a heterobimetallic catalysis, see: Funabashi, K.; Saida, Y.; Kanai, M.; Arai. T.; Sasai, H.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 7557-7558.
14. For a recent review, see: Girard, C.; Kagan, H. B. Angew. Chem., Int. Ed. Engl. 1998, 37, 2922-2959.
15. The ALB complex consisting of a (R)-BINOL and a (S)-BINOL cannot be formed due to steric hindrance.
16. Shimizu, S.; Ohori, K.; Arai, T.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1998, 63, 7547-7551.