trans-Stereoselective intramolecular crossed pinacol coupling of aromatic 1,4-, 1,5-, and 1,6-diketones by electroreduction

Tetrahedron Letters

Volumn 45, Issue 41, 2004, Pages 7599-7603

  Kise, Naoki ^a   Shiozawa, Yousuke ^a   Ueda, Nasuo ^a  

^a TOTTORI UNIVERSITY   (Japan)

Author keywords

1,2 Diols; 1,4 Diketones; 1,5 Diketones; 1,6 Diketones; Crossed pinacol coupling; Electroreduction

Indexed keywords

ALCOHOL DERIVATIVE; AROMATIC COMPOUND; CHLOROTRIMETHYLSILANE; DIKETONE; KETONE DERIVATIVE; TRIETHYLAMINE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CROSS REACTION; MOLECULAR INTERACTION; PINACOL REARRANGEMENT; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 4544228508     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.08.120     Document Type: Article

References (17)

1. H.M.R. Hoffmann, I. Münnich, O. Nowitzki, H. Stucke, and D.J. Williams Tetrahedron 52 1996 11783
2. O. Nowitzki, I. Münnich, H. Stucke, and H.M.R. Hoffmann Tetrahedron 52 1996 11799
3. T. Fujiwara, Y. Tsuruta, K. Arizono, and T. Takeda Synlett 1997 962
4. J. Nakayama, S. Yamaoka, and M. Hoshino Tetrahedron Lett. 28 1987 1799
5. N. Kise, K. Arimoto, and N. Ueda Tetrahedron Lett. 44 2003 6281
6. THF was oxidized at anode to polymeric compounds and these obstructed current supply. Therefore, DMF was employed as the solvent of the anolyte
7. 3): δ -0.26 (s, 6H), -0.10 (s, 3H), -0.08 (s, 6H), 0.19 (s, 3H), 0.87 (s, 1H), 1.45 (s, 2H), 1.73-1.94 (m, 2.33H), 2.01-2.07 (m, 0.33H), 2.27-2.34 (m, 0.33H), 2.39-2.47 (m, 0.33H), 2.53-2.61 (m, 0.67H), 7.19-7.24 (m, 1H), 7.26-7.31 (m, 2H), 7.41-7.45 (m, 2H)
8. 3): δ 21.8 (q), 28.5 (t), 31.6 (t), 77.9 (s), 82.1 (s), 126.6 (d), 127.9 (d), 128.6 (d), 140.1 (s)
9. 3, δ) of these isomers are as follows. trans-5: -0.17 (s, 9H), 0.00 (s, 9H), 1.13 (s, 3H), 1.69-1.91 (m, 4H), 1.97-2.05 (m, 1H), 2.75-2.83 (m, 1H), 7.18-7.22 (m, 1H), 7.23-7.28 (m, 2H), 7.40-7.45 (m, 1H). cis-5: -0.10 (s, 9H), 0.15 (s, 9H), 0.84 (s, 3H), 1.60-1.72 (m, 2H), 1.89-1.98 (m, 1H), 1.99-2.06 (m, 1H), 2.13-2.21 (m, 1H), 2.32-2.39 (m, 1H), 7.20-7.28 (m, 3H), 7.49-7.53 (m, 2H). trans-6: 0.15 (s, 9H), 0.95 (s, 3H), 1.70-1.76 (m, 1H), 1.79-1.85 (m, 1H), 1.97-2.14 (m, 3H), 2.33-2.40 (m, 1H), 3.89 (s, 1H), 7.22-7.33 (m, 3H), 7.43-7.47 (m, 2H). cis-6: -0.03 (S, 9H), 0.81 (S, 3H), 1.70-1.78 (m, 2 H), 1.91-2.02 (m, 2H), 2.14-2.21 (m, 1H), 2.43-2.51 (m, 1H), 3.21 (s, 1H), 7.23-7.32 (m, 3H), 7.42-7.46 (m, 2H)
10. 3): δ 19.4 (t), 20.9 (q), 37.6 (t), 37.8 (t), 82.4 (s), 85.6 (s), 127.0 (d), 127.4 (d), 128.0 (d), 141.2 (s)
11. 3): δ 0.05 (s, 9H), 0.91 (br s, 1H), 1.01 (s, 3H), 1.47-1.77 (m, 6H), 1.88-1.97 (m, 1H), 2.58-2.66 (m, 1H), 7.20-7.35 (m, 3H), 7.47-7.51 (m, 2H)
12. E.P. Balskus, J. Méndez-Andino, R.M. Arbit, and L.A. Paquette J. Org. Chem. 66 2001 6695
13. 3): δ -0.05 (s, 9H), 0.98 (s, 3H), 1.35-1.41 (m, 1H), 1.45 (s, 1H), 1.47-1.80 (m, 5H), 1.83-1.91 (m, 1H), 2.56-2.64 (m, 1H), 7.20-7.25 (m, 1H), 7.26-7.31 (m, 1H), 7.53-7.58 (m, 2H)
14. 3): δ -0.29 (s, 9H), -0.03 (s, 9H), 1.18 (t, 3H, J = 7.1 Hz), 1.38 (s, 3H), 1.72-1.81 (m, 2H), 1.85-1.91 (m, 1H), 2.05-2.13 (m, 1H), 2.53-2.71 (m, 3H), 2.93-3.02 (m, 1H), 3.95-4.02 (m, 1H), 4.14-4.21 (m, 1H), 7.02-7.07 (m, 1H), 7.09-7.14 (m, 2H), 7.36-7.40 (m, 1H)
15. 3): δ -0.02 (s, 3.6H), 0.18 (s, 5.4H), 0.83 (s, 1.8H), 1.18 (t, 1.8H, J = 7.1 Hz), 1.20 (t, 1.2H, J = 7.1 Hz), 1.36 (s, 1.2H), 1.52-1.60 (m, 0.6H), 1.74-1.96 (m, 2.4H), 2.04-2.26 (m, 1.6H), 2.49-2.76 (m, 2.4H), 2.89-3.04 (m, 1H), 4.00-4.24 (m, 2H), 7.05-7.09 (m, 0.6H), 7.11-7.22 (m, 2.4H), 7.44-7.49 (m, 1H)
16. 3): δ 0.11 (s, 9H), 0.78 (s, 1H), 1.04 (t, 3H, J = 7.3 Hz), 1.10 (s, 3H), 1.48-1.68 (m, 3H), 1.76-1.99 (m, 3H), 2.10-2.18 (m, 1H), 2.78-2.91 (m, 2H), 3.23-3.32 (m, 1H), 0.01 (m, 2H), 7.03-7.07 (m, 1H), 7.12-7.17 (m, 2H), 7.38-7.42 (m, 2H)
17. -1, GOF = 1.002