Construction of chiral quaternary carbon centers by asymmetric alkylation of achiral lithium enolates mediated by chiral tetradentate ligands: Stoichiometric and catalytic approaches

Tetrahedron Letters

Volumn 40, Issue 14, 1999, Pages 2803-2806

  Yamashita, Yasuhiro ^a   Odashima, Kazunori ^a   Koga, Kenji ^a,b  

^a UNIVERSITY OF TOKYO   (Japan)

^b NARA INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

Author keywords

Asymmetric synthesis Enantioselection; Catalysis; Quaternization

Indexed keywords

CARBON; LIGAND; LITHIUM;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; REACTION ANALYSIS; STOICHIOMETRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033515721     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00299-3     Document Type: Article

References (22)

1. For reviews, see: a) Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 1624-1654.
2. b) Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopadhyay, T.; Simson, M.; Seebach, D. Synthesis 1993, 1271-1290.
3. c) Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; John Wiley & Sons: New York, 1995; Chapter 5.3 (pp 166-188).
4. d) Berrisford, D. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 178-180.
5. e) Koga, K. Pure Appl. Chem. 1994, 66, 1487-1492.
6. f) Koga, K.; Shindo, M. J. Synth. Org. Chem., Jpn. 1995, 53, 1021-1032.
7. a) Murakata, M.; Nakajima, M.; Koga, K. J. Chem. Soc., Chem. Commun. 1990, 1657-1658.
8. b) Hasegawa, Y.; Kawasaki, H.; Koga, K. Tetrahedron Lett. 1993, 34, 1963-1966.
9. c) Imai, M.; Hagihara, A.; Kawasaki, H.; Manabe, K.; Koga, K. J. Am. Chem. Soc. 1994, 116, 8829-8830.
10. d) Matsuo, J.; Koga, K. Chem. Pharm. Bull. 1997, 45, 2122-2124.
11. e) Murakata, M.; Yasukata, T.; Aoki, T.; Nakajima, M.; Koga, K. Tetrahedron 1998, 54, 2449-2458.
12. f) Uragami, M.; Tomioka, K.; Koga, K. Tetrahedron: Asymmetry 1995, 6, 701-704.
13. g) Yasuda, K.; Shindo, M.; Koga, K. Tetrahedron Lett. 1996, 37, 6343-6346.
14. h) Yasuda, K.; Shindo, M.; Koga, K. Tetrahedron Lett. 1997, 38, 3531-3534.
15. i) Yasukata, T.; Koga, K. Tetrahedron: Asymmetry 1993, 4, 35-38.
16. j) Riviere, P.; Koga, K. Tetrahedron Lett. 1997, 38, 7589-7592.
17. 4, filtered and evaporated to give the crude product, which was purified by column chromatography (silica gel, hexane-ether 50:1) to give a mixture of the target compound and the ketone derived from the starting TMS enol ether. The mixture was analyzed by HPLC using a chiral column (Daicel Chiralcel OJ® or ODH®) to determine the enantiomeric excess and the chemical yield using naphthalene as an internal standard.
18. d Polyphosphoric acid
19. Tomioka, K.; Cho, Y.-S.; Sato, F.; Koga, K. J. Org. Chem. 1988, 53, 4094-4098.
20. For reviews on diastereo- and enantioselective construction of chiral quaternary carbon centers, see: a) Martin, S. F. Tetrahedron 1980, 36, 419-460.
21. b) Fuji, K. Chem. Rev. 1993, 93, 2037-2066.
22. c) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. Engl. 1998, 37, 388-401.