A new stereospecific synthesis of unusual (Z)-β-branched Baylis- Hillman adducts

Tetrahedron Letters

Volumn 39, Issue 26, 1998, Pages 4607-4610

  Li, Guigen ^a   Wei, Han Xun ^a   Willis, Steven ^a  

^a TEXAS TECH UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; KETONE;

ARTICLE; CHIRALITY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOSPECIFICITY; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 0032565841     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00850-8     Document Type: Article

References (18)

1. 1. Baylis-Hillman reaction is also referred as Morita-Baylis-Hillman reaction in reference 3.
2. 2. Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001.
3. 3. Ciganek, E. Org. React., 1997, 51, 201, and references therein.
4. 4. Brzezinski, L. J.; Rafel, S.; Leahy, J. M. J. Am. Chem. Soc. 1997, 119, 4317.
5. 5. Marko, I. E.; Giles, P. G.; Hindley, N. J. Tetrahedron 1997, 53, 1015.
6. 6. Aggarwal, V.; Tarver, G. J.; McCague, R. J. Chem. Soc. Chem. Commun. 1996, 2713.
7. 7. (a) Genisson, Y.; Massardier, C.; Gautier-Luneau, I.; Greene, A. E. J. Chem. Soc. Perkin Trans. I 1996, 2860;
8. (b) Xu, L.-H.; Kundig, E. P. Helv. Chim. Acta 1994, 77, 1480. For intramolecular Baylis-Hillman reaction see 8 and 9.
9. 8. Roth, F.; Gygax, P.; Frater, G. Tetrahedron Lett. 1992, 48, 6371.
10. 9. Drewes, S. E.; Njamela, O. L.; Emslie, N. D.; Ramesar, N.; Field, J. S. Synth. Coomun. 1993, 23, 2807.
11. 10. Sato, Y.; Takeuchi, S. Synthesis, 1983, 734.
12. 11. Marino, J. P.; Linderman, R. J. J. Org. Chem. 1983, 48, 4621.
13. 12. Tsuda, T.; Yoshida, T.; Saegusa, T. J. Org.Chem. 1988, 53, 1037.
14. 13. Tsuda, T.; Yoshida, T.; Kawamoto, T.; Saegusa, T. J. Org. Chem. 1987, 52, 1624.
15. 2BOTf (2 mol%, 5 mol%) were able to catalyze the reaction in the similar condition, but gave lower yields.
16. 3): 2 δ 1.11 (t, J = 7.1 Hz, 3 H), 1.47 (d, J = 6.5 Hz, 3 H), 2.45 (d, J = 5.9 Hz, 1 H), 4.16 (dd, J = 14.2 Hz, 8.1 Hz, 2 H), 4.65 (m, 1 H), 6.70 (s, 1 H), 7.26 - 7.31 (m, 5 H); 3 δ 1.04 (t, J = 7.2 Hz, 3 H), 3.16 (d, J = 7.2 Hz, 1 H), 4.10 (dd, J = 14.4 Hz, 7.1 Hz, 2 H), 5.60 (dd, J = 7.2 Hz, 1.2 Hz, 1 H), 6.35 (d, J = 1.2 Hz, 2 H), 7.04 (d, J = 1.0 Hz, 1 H), 7.29 - 7.31 (m, 5 H), 7.41 (t, J = 1.2 Hz, 1 H); 4 δ 1.09 (t, J = 7.0 Hz, 3 H), 1.74 (d, J = 6.1 Hz, 3 H), 2.57 (d, J = 6.7 Hz, 1 H), 4.14 (dd, J = 15.0 Hz, 7.1 Hz, 2 H), 4.93 (m, 1 H), 5.59 - 5.92 (m, 2 H), 6.91 (d, J = 0.9 Hz, 1 H), 7.25 - 7.45 (m, 5 H); 5 δ 0.81 (t, J = 7.1 Hz, 3 H). 1.78 (s, 3 H), 3.90 (m, 2 H), 4.15 (s, 1 H), 7.03 (s, 1 H), 7.24 - 7.53 (m, 10 H); 6 δ 1.18 (t, J = 7.1 Hz, 3 H), 2.05 (d, J = 7.5 Hz, 3 H), 3.22 (d, J = 7.2 Hz, 1 H), 4.14 (dd, J = 14.3 Hz, 7.2 Hz, 2 H), 5.42 (d, J = 7.0 Hz, 1 H), 6.31 (dd, J = 14.5 Hz, 7.0 Hz, 2 H), 7.25 - 7.35 (m, 5 H); 7 δ 1.34 (t, J = 6.6 Hz, 3 H), 2.01 (d, J = 7.1 Hz, 3 H), 2.69 (d, J = 6.7 Hz, 1 H), 4.28 (dd, J = 7.1 Hz, 1.6 Hz, 2 H), 4.48 (m, 1 H), 6.29 (dd, J = 7.1 Hz, 0.8 Hz, 1 H); 8 δ 1.26 (t, J = 7.1 Hz, 3 H), 2.08 (d, J = 7.4 Hz, 3 H), 3.29 (d, J = 7.9 Hz, 1 H), 4.22 (dd, J = 14.3 Hz, 7.1 Hz, 2 H), 5.43 (d, J = 7.6 Hz, 1 H), 6.23 - 6.42 (m, 3 H), 7.35 - 7.37 (m, 1 H); 10 δ 1.26 (t, J = 7.1 Hz, 3 H), 1.60 (s, 3 H), 2.32 (d, J = 1.4 Hz, 3 H), 4.10 (s, 1 H), 4.20 (dd, J = 7.1 Hz, 2.5 Hz, 2 H), 6.70 (d, J = 1.2 Hz, 1 H), 7.20 - 7.87 (m, 5 H).
17. 16. (a) Li, G.; Wei, H.-X,; Willis, S. SYNLETT submitted;
18. (b) Li, G.; Wei, H.-X.; Willis, S. to be submitted.