Enantioselective aromatic Claisen rearrangement

Tetrahedron Letters

Volumn 38, Issue 27, 1997, Pages 4815-4818

  Ito, Hisanaka ^a   Sato, Azusa ^a   Taguchi, Takeo ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BORON DERIVATIVE; CATECHOL DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031008023     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01040-X     Document Type: Article

References (18)

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4. d) Bennett, G. B. Synthesis 1977, 589-606.
5. e) Ziegler, F. E. Chem. Rev. 1988, 88, 1426-1452.
6. f) Blechert, S. Synthesis 1989, 71-82.
7. a) Maruoka, K.; Banno, H.; Yamamoto, H. J. Am. Chem. Soc. 1990, 112, 7791-7793.
8. b) Maruoka, K.; Banno, H.; Yamamoto, H. Tetrahedron:Asymmetry 1991, 2, 647-662.
9. c) Maruoka, K.; Yamamoto, H. Synlett 1991, 793-794.
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11. a) Corey, E. J.; Lee, D.-H. J. Am. Chem. Soc. 1991, 113, 4026-4028.
12. b) Corey, E. J.; Kania, R. S. J. Am. Chem. Soc. 1996, 118, 1229-1230.
13. Kazmaier, U.; Krebs, A. Angew. Chem. Int. Ed. Engl. 1995, 34, 2012-2014.
14. See reference 1a.
15. The catechol mono allylic ether derivatives could be easily prepared from mono protected catechol derivatives with commercially available allylic alcohol by Mitsunobu reaction and following deprotection.
16. D value with that of authentic sample. The procedure for preparing authentic sample is shown in Scheme 2. Scheme 2 (formula presented)
17. H NMR of the reaction mixture.
18. 3 at room temperature. The chemical shift of the methoxy group shifted to higher field by 0.44 ppm (2-methoxyphenol; 3.89 ppm, chiral complex; 3.45 ppm), possibly due to the anisotropic effect of the tolyl group through the coordination of methoxy oxygen to the boron atom.