Proline-catalyzed aldol reactions of acyl cyanides with acetone: An efficient and convenient synthesis of 1,3-diketones

Tetrahedron Letters

Volumn 46, Issue 50, 2005, Pages 8785-8788

  Shen, Zongxuan ^a   Li, Bin ^a   Wang, Lu ^a   Zhang, Yawen ^a  

^a SOOCHOW UNIVERSITY   (China)

Author keywords

1,3 Diketones; Acetone; Acyl cyanides; Addition; Proline

Indexed keywords

1,3 DIKETONE; ACETONE; CYANIDE; PROLINE; SODIUM HYDROXIDE;

ALDOL REACTION; ARTICLE; SUBSTITUTION REACTION; SYNTHESIS;

EID: 27744553040     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.10.036     Document Type: Article

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14. 3): δ 2.31 (s, 3H), 2.85 (d, J = 18.4 Hz, 1H), 3.93 (d, J = 18.4 Hz, 1H), 5.83 (s, 1H), 7.33-7.40 (m, 2H), 7.44 (d, J = 7.2 Hz, 1H), 7.83 (d, J = 7.6 Hz, 1H).
15. 3): δ 2.13-2.15 (m, 6H), 3.25 (d, J = 17.2 Hz, 1H), 3.45 (d, J = 17.2 Hz, 1H), 7.38-7.44 (m, 3H), 7.54 (d, J = 7.6 Hz, 2H).
16. 13C NMR, and HRMS spectroscopy.
17. 3): δ 1.87-1.94 (m, 1H), 2.00-2.09 (m, 1H), 2.23-2.29 (m, 1H), 2.33-2.39 (m, 1H), 3.59 (t, J = 6.8 Hz, 2H), 4.56 (br s, 1H), 4.76 (dd, J = 7.6, 4.8 Hz, 1H), 7.38-7.58 (m, 5H).
18. K. Sakthivel, W. Notz, T. Bui, and C.F. Barbas III J. Am. Chem. Soc. 123 2001 5260 5267
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