Preparation of a Promising Cyclobutanone Chiral Building Block: Its Stereochemistry and Utilization

Synlett

Volumn 1997, Issue 6, 1997, Pages 707-709

  Taniguchi, Takahiko ^a   Goto, Yasuo ^a   Ogasawara, Kunio ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001459417     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-3270     Document Type: Article

References (27)

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2. Hegedus, L. S. Acc. Chem. Res. 1995, 28, 299; Brady, W. T. Synthesis 1971, 415; Brady, W. T. Tetrahedron 1981, 37, 2949; Ghosez, L. Tetrahedron 1989, 45, 2875; Lee-Ruff, E. "New Synthetic Pathways from Cyclobutanones" Halton B. Ed. Jai Press, Greenwich, 1991, 1; Moore, H. W.; Gheorghina, M. D. Chem. Soc. Rev. 1981, 10, 289.
3. Hegedus, L. S. Acc. Chem. Res. 1995, 28, 299; Brady, W. T. Synthesis 1971, 415; Brady, W. T. Tetrahedron 1981, 37, 2949; Ghosez, L. Tetrahedron 1989, 45, 2875; Lee-Ruff, E. "New Synthetic Pathways from Cyclobutanones" Halton B. Ed. Jai Press, Greenwich, 1991, 1; Moore, H. W.; Gheorghina, M. D. Chem. Soc. Rev. 1981, 10, 289.
4. Hegedus, L. S. Acc. Chem. Res. 1995, 28, 299; Brady, W. T. Synthesis 1971, 415; Brady, W. T. Tetrahedron 1981, 37, 2949; Ghosez, L. Tetrahedron 1989, 45, 2875; Lee-Ruff, E. "New Synthetic Pathways from Cyclobutanones" Halton B. Ed. Jai Press, Greenwich, 1991, 1; Moore, H. W.; Gheorghina, M. D. Chem. Soc. Rev. 1981, 10, 289.
5. Hegedus, L. S. Acc. Chem. Res. 1995, 28, 299; Brady, W. T. Synthesis 1971, 415; Brady, W. T. Tetrahedron 1981, 37, 2949; Ghosez, L. Tetrahedron 1989, 45, 2875; Lee-Ruff, E. "New Synthetic Pathways from Cyclobutanones" Halton B. Ed. Jai Press, Greenwich, 1991, 1; Moore, H. W.; Gheorghina, M. D. Chem. Soc. Rev. 1981, 10, 289.
6. Hegedus, L. S. Acc. Chem. Res. 1995, 28, 299; Brady, W. T. Synthesis 1971, 415; Brady, W. T. Tetrahedron 1981, 37, 2949; Ghosez, L. Tetrahedron 1989, 45, 2875; Lee-Ruff, E. "New Synthetic Pathways from Cyclobutanones" Halton B. Ed. Jai Press, Greenwich, 1991, 1; Moore, H. W.; Gheorghina, M. D. Chem. Soc. Rev. 1981, 10, 289.
7. For a pertinent review, see: Ogasawara, K. J. Syn. Org. Chem. Jpn. 1996, 54, 15.
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12. A pertinent monogragh, see: Wong, C. -H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry, Pergamon: Oxford, 1994.
13. Optical purity was determined by a hplc using chiral column (CHIRALCEL OD, elution with 2% i-PrOH-hexane) after transformation of the alcohol 2 into its benzoate.
14. 6) as a colorless oil.
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16. A pertinent review, see: Takano, S.; Ogasawara, K. J. Syn. Org. Chem. Jpn. 1977, 35, 795.
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21. ( 14) Stork, G.; Zhao, K. Tetrahedron Lett. 1989, 30, 287.
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23. Arai, Y; Kawanami, S.; Koizumi, T. Chem. Lett. 1990, 1585. idem J. Chem. Soc., Perkin Trans. 1 1991, 2969.
24. Arai, Y; Kawanami, S.; Koizumi, T. Chem. Lett. 1990, 1585. idem J. Chem. Soc., Perkin Trans. 1 1991, 2969.
25. Chiral syntheses of boschnialactone, see: For the unnatural (+)-enantiomer: Tanaka, D.; Yoshino, T.; Kouno, I.; Miyashita, M.; Irie, H. Tetrahedron 1993, 49, 10253 . For the natural (-)-enantiomer; Nangia, A.; Prasuna, G.; Rao, P. B. Tetrahedron Lett. 1994, 35, 3755.
26. Chiral syntheses of boschnialactone, see: For the unnatural (+)-enantiomer: Tanaka, D.; Yoshino, T.; Kouno, I.; Miyashita, M.; Irie, H. Tetrahedron 1993, 49, 10253 . For the natural (-)-enantiomer; Nangia, A.; Prasuna, G.; Rao, P. B. Tetrahedron Lett. 1994, 35, 3755.
27. Sakan, T; Murai, F.; Hayashi, Y.; Honda, Y.; Shono, T.; Nakajima, M.; Kato, M. Tetrahedron 1967, 23, 4635.