Preparation and utility of novel water-tolerant higher-order lanthanoid alkoxide complexes as a base catalyst

Chemistry Letters

Volumn , Issue 7, 1998, Pages 697-698

  Kamaura, Masahiro ^a   Daikai, Kazuhiro ^a   Hanamoto, Takeshi ^a   Inanaga, Junji ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0032380839     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1998.697     Document Type: Article

References (16)

1. Some examples: a) S. Kobayashi, Synlett, 1994, 689.
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4. For an excellent review: see, R. Anwander, in "Topics in Current Chemistry," ed by W. A. Herrmann, Springer, Berlin-Heidelberg-New York (1996), Vol. 179, p. 149.
5. Some examples: a) T. Okano, M. Matsuoka, H. Konishi, and J. Kiji, Chem. Lett., 1987, 181.
6. b) A. Lebrun, J. L. Namy, and H. B. Kagan, Tetrahedron Lett., 32, 2355 (1991).
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11. g) T. Okano, Y. Satou, M. Tamura, and J. Kiji, Bull. Chem. Soc. Jpn., 70, 1879 (1997).
12. J.-M. Lehn, "Supramolecular Chemistry," VCH, Weinheim (1995).
13. + ions as co-cations have been prepared and successfully used in a variety of asymmetric syntheses: a) M. Shibasaki, H. Sasai, and T. Arai, Angew. Chem., Int. Ed. Engl., 36, 1236 (1997) and references cited therein.
14. 3g
15. Presented at the 74th Meeting of the Chemical Society of Japan, Kyoto, March, 1998.
16. 3 (12.1 mg, 0.02 mmol) in THF (1 ml) was added a hexane solution of n-BuLi (1.58 M, 76 μl, 0.12 mmol). After stirring for 30 min at room temperature, a THF solution of polyethylene glycol (mol. wt. ca. 200, 10.7 μl, 0.06 mmol) was added and the mixture was stirred further for 1 h. To this mixture was added a solution of chalcone (41.6 mg, 0.2 mmol) and 2-butanone (180 ml, 2.0 mmol) in THF (1 ml) and the whole mixture was stirred for 48 h at 50°C. The reaction mixture was passed through a short column of silica gel. After evaporation of the solvent, the crude product was purified by preparative TLC (hexane/AcOEt=10/1, two times development) to give 3,5-diphenyl-6-methyl-2-cyclohexen-1-one (49.3 mg, 94%) as a diastereomeric mixture (81:19).