Regioselectivity in the reduction of cyclic enediones with NaBH4/CeCl3

Tetrahedron Letters

Volumn 38, Issue 37, 1997, Pages 6573-6576

  Liu, Chunjian ^a   Burnell, D Jean ^a  

^a MEMORIAL UNIVERSITY OF NEWFOUNDLAND   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CERIUM; POLYCYCLIC AROMATIC HYDROCARBON; SODIUM BOROHYDRIDE;

ARTICLE; COMPLEX FORMATION; REDUCTION; STEREOCHEMISTRY;

EID: 0030750994     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01498-6     Document Type: Article

References (11)

1. Liu, C.; Burnell, D. J. J. Org. Chem. 1997, 62, 3683-3687.
2. Regioselectivity in the reactions of enediones toward lithium acetylide was previously examined by: Liotta, D.; Saindane, M.; Sunay, U.; Jamison, W. C. L.; Grossman, J.; Phillips, P. J. Org. Chem. 1985, 50, 3243-3245.
3. For some examples of selectivity in synthetic applications: (a) Das, J.; Kubela, R.; MacAlpine, G. A.; Stojanac, Z.; Valenta, Z. Can. J. Chem. 1979, 57, 3308-3319.
4. (b) Kienzle, F.; Stadlweiser, J.; Rank, W.; Schönholzer, P. Helv. Chim. Acta 1990, 73, 1108-1138.
5. (c) Nampalli, S.; Bhide, R. S.; Nakai, H. Synth. Commun. 1992, 22, 1165-1177.
6. (d) Khan, N.; Larsen, L.; Sutherland, J. K. Tetrahedron 1993, 49, 8233-8240.
7. 3 was an isolated example reported by: Ishihara, M.; Tsuneya, T.; Shiota, H.; Shiga, M.; Nakatsu, K. J. Org. Chem. 1986, 51, 491-495.
8. 4 and concentrated under vacuum. Flash chromatography provided 9, 10, and 11 in a total yield of 90%.
9. 13C NMR δ 202.0 (0), 180.0 (0), 142.2 (1), 140.0 (0), 134.9 (0), 116.8 (0), 81.7 (1), 67.3 (1), 52.0 (1), 49.9 (1), 48.5 (1), 45.9 (0), 42.2 (1), 33.3 (2), 30.9 (2), 25.6 (4C, 3), 25.5 (3), 18.0 (0), 16.1 (3), -3.9 (3), -4.1 (3).
10. 3 was exploited synthetically by: Trost, B. M.; Tometzki, G. B. J. Org. Chem. 1988, 53, 915-917.
11. Molander, G. A. Chem. Rev. 1992, 92, 29-68, and references therein.