Importance of the hydroxymethyl - Quinuclidine fragment in the catalytic asymmetric aldol reactions utilizing quaternary ammonium fluorides derived from cinchona alkaloids

Heterocycles

Volumn 42, Issue 1, 1996, Pages 93-97

  Shioiri, Takayuki ^a   Bohsako, Akemi ^a,b   Ando, Akira ^a,c  

^a NAGOYA CITY UNIVERSITY   (Japan)

^b KAKEN PHARMACEUTICAL CO LTD   (Japan)

^c MITSUBISHI TANABE PHARMA CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002213288     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-95-S28     Document Type: Article

References (8)

1. A. Ando, T. Miura, T. Tatematsu, and T. Shioiri, Tetrahedron Lett., 1993, 34, 1507.
2. For fluoride catalyzed aldol reactions between enol silyl ethers and carbonyl compounds, see E. Nakamura, M. Shimizu, I. Kuwajima, J. Sakata, K. Yokoyama, and R. Noyori, J. Org. Chem., 1983, 48, 932.
3. Quaternary ammonium fluorides derived from cinchonine were used for asymmetric catalytic trifluoromethylation of aldehydes and ketones. See K. Iseki, T. Nagai, and Y. Kobayashi, Tetrahedron Lett., 1994, 35, 3137.
4. D. Landini, H. Molinari, M. Penso, and A. Rampoldi, Synthesis, 1988, 953.
5. D. L. Hughes, U. -H. Dolling, K. M. Ryan, E. F. Schoenewaldt, and E. J. J. Grabowski, J. Org. Chem., 1987, 52, 4745.
6. M. Masui, A. Ando, and T. Shioiri, Tetrahedron Lett., 1988, 29, 2835.
7. K. B. Lipkowitz, M. W. Cavanaugh, B. Baker, and M. J. O'Donnell, J. Org. Chem., 1991, 56, 5181.
8. M. J. O'Donnell, S. Wu, and J. C. Huffman, Tetrahedron, 1994, 50, 4507.