Efficient Baylis-Hillman reactions promoted by mild cooperative catalysts and their application to catalytic asymmetric synthesis

Tetrahedron Letters

Volumn 41, Issue 13, 2000, Pages 2165-2169

  Yamada, Yoichi M A ^a   Ikegami, Shiro ^a  

^a TEIKYO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANONE; NAPHTHOL DERIVATIVE; PHENOL DERIVATIVE; PHOSPHINE DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 0034719742     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00125-8     Document Type: Article

References (30)

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2. For reviews, see: (a) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653-4670. (b) Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001-8062. (c) Ciganek, E. Org. React. 1997, 51, 201-350.
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9. Recently, Hatakeyama et al. reported catalytic asymmetric Baylis-Hillman reactions of 1,1,1,3,3,3-hexafluoro-isopropyl acrylate. Iwabuchi, Y.; Nakatani, M.; Yokoyama, N.; Hatakeyama, S. J. Am. Chem. Soc. 1999, 121, 10219-10220.
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28. 2 (120.6 mg; 0.762 mmol) (purchased from High Purity Chemicals Lab. Co., Ltd) in THF (7.65 ml) was added a solution of (R)-1,1′-bi-2-naphthol (327.3 mg; 1.14 mmol) in THF (11.4 ml) at room temperature, and the mixture was stirred overnight at the same temperature. THF was evaporated under reduced pressure, the residue was dried in vacuo for 4 h, THF (19.5 ml) was again added under an argon atmosphere, and the suspension was allowed to stand for several hours to give a solution of the catalyst.
29. The enantiomeric excess of 3a was determined by HPLC analysis (Daicel Chiralpak AS; detection at 254 nm; eluent: 2-propanol/hexane (1/9)), and the absolute configuration was determined by Mosher's method after conversion to (2R*)-2-((1S*)-1-hydroxy-3-phenylpropyl)cyclopentanone. For Mosher's method, see: Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-519.
30. This result might indicate that the calcium catalyst has been self-assembled with 4. For self-assembly of heterobimetallic catalyst and reactive nucleophiles, see: Shimizu, S.; Ohori, K.; Arai, T.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1998, 63, 7547-7551, and references cited therein.