A new method for the synthesis of unsymmetrical bis-aldols by the samarium(II) iodide-mediated aldol reaction of aldehydes with aryl or alkyl oxiranyl ketones

Chemistry Letters

Volumn , Issue 5, 2000, Pages 580-581

  Mukaiyama, Teruaki ^a   Arai, Hidehiro ^a   Shiina, Isamu ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0034335919     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2000.580     Document Type: Article

References (9)

1. B. M. Trost and I. Fleming, "Comprehensive Organic Synthesis," Pergamon Press, Oxford (1991), Vol. 2.
2. Morris et al. reported two examples of bis-aldol formation by the reaction of alkyl 2-hydroxyalkyl ketones and 2-methylpropanal using I molar amount of dichlorophenylborane or trichloroborane and 2 molar amounts of ethyldiisopropylamine. G. P. Luke and J. Morris, J. Org. Chem., 60, 3013 (1995), See also: P. A. McCarthy and M. Kageyama, J. Org. Chem., 52, 4681 (1987).
3. Morris et al. reported two examples of bis-aldol formation by the reaction of alkyl 2-hydroxyalkyl ketones and 2-methylpropanal using I molar amount of dichlorophenylborane or trichloroborane and 2 molar amounts of ethyldiisopropylamine. G. P. Luke and J. Morris, J. Org. Chem., 60, 3013 (1995), See also: P. A. McCarthy and M. Kageyama, J. Org. Chem., 52, 4681 (1987).
4. A. Abiko, J.-F. Liu, D. C. Buske, S. Moriyama, and S. Masamune, J. Am. Chem. Soc., 121, 7168 (1999).
5. T. Mukaiyama and T. Inoue, Chem. Lett., 1976, 559.
6. G. A. Molander and G. Hahn, J. Org. Chem., 51, 1135 (1986).
7. 2, which in turn reacted with carbonyl compounds to form the corresponding aldol-type products. S. Ichikawa, S. Shuto, and A. Matsuda, Tetrahedron Lett., 39, 4525 (1998).
8. G. A. Molander and G. Hahn, J. Org. Chem., 51, 2596 (1986).
9. T. Katsuki and K. B. Sharpless, J. Am. Chem. Soc., 102, 5974 (1980).