Enantioselective methylation of the lithium enolate of 1-tetralone mediated by chiral C2-symmetric DMEU derivatives

Tetrahedron Letters

Volumn 38, Issue 4, 1997, Pages 563-566

  Ishii, Katsuyuki ^a,c   Aoki, Shin ^b,c   Koga, Kenji ^c  

^a ZERIA PHARMACEUTICAL CO LTD   (Japan)

^b HIROSHIMA UNIV SCHOOL OF MEDICINE   (Japan)

^c UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOLITHIUM COMPOUND; TETRALIN DERIVATIVE; UREA DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; METHYLATION; REACTION ANALYSIS;

EID: 0031023037     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02372-6     Document Type: Article

References (16)

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3. c) Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 1624-1654.
4. Systematic IUPAC name is 1,3-dimethyl-2-oxo-hexahydropyrimidine.
5. Systematic IUPAC name is 1,3-dimethyl-2-imidazolidinone.
6. a) Mukhopadhyay, T.; Seebach, D. Helv. Chim. Acta 1982, 65, 385-391.
7. b) Seebach, D.; Henning, R.; Mukhopadhyay, T. Chem. Ber. 1982, 115, 1705-1720.
8. c) Seebach, D.; Beck, A. K.; Studer, A. in Modern Synthetic Methods 1995, Vol. 7, ed. by Ernst, B.; Leumann, C: VCH, 1995, p. 1-178.
9. a) Murakata, M.; Nakajima, M.; Koga, K. J. Chem. Soc., Chem. Commun. 1990, 1657-1658.
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11. c) Koga, K.; Shindo, M. J. Synth. Org. Chem., Jpn. 1995, 53, 1021-1032.
12. 1H-NMR, MS, and elemental analyses.
13. 2.
14. The absolute configuration of optically active 3 is known: Jaouen, G.; Meyer, A. J. Am. Chem. Soc. 1975, 97, 4667-4672.
15. For example, see: Corey, E. J.; Yu, C-M.; Kim, S. S. J. Am. Chem. Soc. 1989, 111, 5495-5496.
16. It is shown by X-ray analysis that the conformation of 5 in a solid state is as expected. Details will be reported elsewhere.