Single-chiral bis(oxazolinyl)pyridine (pybox). Efficiency in asymmetric catalytic cyclopropanation

Tetrahedron Asymmetry

Volumn 9, Issue 16, 1998, Pages 2865-2869

  Nishiyama, Hisao ^a   Soeda, Norikazu ^a   Naito, Tomonari ^a   Motoyama, Yukihiro ^a  

^a TOYOHASHI UNIVERSITY OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CYCLOPROPANE; LIGAND; RUTHENIUM; STYRENE DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; ENANTIOMER; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032555680     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00303-6     Document Type: Article

References (14)

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2. (b) R. Noyori, Asymmetric Catalysis in Organic Synthesis, John Wiley and Sons, Inc., New York, 1994, p. 199.
3. (c) L. Seyden-Penne, Chiral Auxiliaries and Ligands in Asymmetric Synthesis, John Wiley & Sons, Inc., New York, 1995.
4. (d) M. P. Doyle, Advances in Catalytic Processes, Vol. 2, JAI Press, London, 1997.
5. (e) A. K. Ghosh, P. Mathivanan, J. Cappiello, Tetrahedron: Asymmetry, 1998, 9, 1.
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8. (a) H. Nishiyama, Y. Itoh, H. Matsumoto, S.-B. Park, K. Itoh, J. Am. Chem. Soc., 1994, 116, 2223.
9. (b) H. Nishiyama, Y. Itoh, Y. Sugawara, H. Matsumoto, K. Aoki, K. Itoh, Bull. Chem. Soc. Jpn, 1995, 68, 1247 and references cited therein.
10. (a) S.-B. Park, N. Sakata, H. Nishiyama, Chem. Eur. J., 1996, 2, 303.
11. (b) H. Nishiyama, K. Aoki, H. Itoh, T. Iwamura, N. Sakata, O. Kurihara, Y. Motoyama, Chem. Lett., 1996, 1071.
12. 2, is a more stable isomer than the other isomer having a 90° angle on the basis of extended Hückel calculation.
13. The cyclopropanation with the diazoacetate 3h and styrene did not proceed under the same condition at 60°C for entry 8.
14. We also confirmed that complex 8 acts as a catalyst of the cyclopropanation described above.