Asymmetric Electrophilic Substitution on Phenols. 1. Enantioselective Ortho-Hydroxyalkylation Mediated by Chiral Alkoxyaluminum Chlorides

Journal of Organic Chemistry

Volumn 50, Issue 25, 1985, Pages 5018-5022

  Bigi, Franca ^a   Casiraghi, Giovanni ^a   Casnati, Giuseppe ^a   Sartori, Giovanni ^a   Fava, Giovanna Gasparri ^b   Belicchi, Marisa Ferrari ^b  

^a UNIVERSITY OF PARMA   (Italy)

^b CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845378131     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00225a003     Document Type: Article

References (14)

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2. Casnati, G.; Casiraghi, G.; Pochini, A.; Sartori, G.; Ungaro, R. Pure Appl. Chem. 1983, 55, 1677.
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4. Bigi, F.; Casiraghi, G.; Casnati, G.; Sartori, G. J. Chem. Soc., Chem. Commun. 1983, 1210.
5. For previous work on the use of chiral aluminum compounds in asymmetric synthesis see for example: Natta, G.; Farina, M.; Peraldo, M.; Bressan, G. Makromol. Chem. 1961, 43, 68; Hashimoto, S.; Komeshima, N.; Koga, K. J. Chem. Soc., Chem. Commun. 1979, 437; Samaddar, A. K.; Konar, S. K.; Nasiguri, D. J. Chem. Soc., Perkin Trans. 1 1983, 1449; Giacomelli, G.; Lardicci, L.; Palla, F. J. Org. Chem. 1984, 49, 310. (6) Yamaguchi, S. In “Asymmetric Synthesis”; Morrison, J. D., Ed.; Academic Press: New York, 1983; Vol 1, Chapter 7.
6. For a recent application of this methodology see: Bigi, F.; Casiraghi, G.; Casnati, G.; Sartori, G.; Soncini, P.; Gasparri Fava, G.; Ferrari Belicchi, M. Tetrahedron Lett. 1985, 26, 2021.
7. Corey, E. J.; Ensley, H. E. J. Am. Chem. Soc. 1975, 97, 6908.
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11. Sheldrick, G. M. “shelx-76”, Program for Crystal Structure Determination, University of Cambridge: England, 1976.
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