Efficient catalytic enantioselective Mannich-type reactions using a zirconium-bis(binaphthol)methane complex

Tetrahedron Letters

Volumn 40, Issue 11, 1999, Pages 2161-2164

  Ishitani, Haruro ^a,b   Kitazawa, Takayuki ^a,b   Kobayashi, Shu ^a,b  

^a UNIVERSITY OF TOKYO   (Japan)

^b TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

METHANE; ZIRCONIUM DERIVATIVE;

ARTICLE; CATALYSIS; COMPLEX FORMATION; ENANTIOMER; SYNTHESIS;

EID: 0033548593     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00138-0     Document Type: Article

References (11)

1. (a) E. F. Kleinman, in "Comprehensive Organic Synthesis," eds by B. M. Trost and I. Fleming, Pergamon, Oxford (1991), Vol. 2, p. 893.
2. (b) "Enantioselective Synthesis of β-Amino Acids," ed by E. Juaristi, Wiley-VCH, Weinheim (1996).
3. (a) Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153-7154.
4. (b) Kobayashi, S.; Ueno, M.; Ishitani, H. J. Am. Chem. Soc. 1998, 120, 431-432.
5. H. Ishitani, S. Kobayashi, Tetrahedron Lett. 1996, 37, 7357-7360.
6. Chiral zirconium catalyst 5 was also indicated by modeling studies. Details will be reported in due course.
7. Vogl, E. M.; Matsunaga, S.; Kanai, M.; Iida, T.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 7917-7920.
8. (a) Bougauchi, M.; Watanabe, S.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1997, 119, 2329-2330.
9. (b) Cox, P. J.; Wang, W.; Snieckus, V. Tetrahedron Lett. 1992, 33, 2253-2256.
10. 2a Catalyst 1 gave lower yield when using toluene as a solvent at -45 °C (34% yield, 88% ee).
11. NMI (30 mol%) was used in these cases.