The study of Lewis acid effect on asymmetric Diels-Alder reactions of new 2-sulfinylbutadienes derived from (1R, 2S, 3R)-3-mercaptocamphan-2-ol

Tetrahedron Letters

Volumn 37, Issue 26, 1996, Pages 4537-4540

  Yang, Teng Kuei ^a   Chu, Han Yang ^a   Lee, Dong Sheng ^a,b   Jiang, Yao Zhong ^b   Chou, Ta Shue ^c  

^a NATIONAL CHUNG HSING UNIVERSITY   (Taiwan)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

^c INSTITUTE OF CHEMISTRY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; DIASTEREOISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOSPECIFICITY;

BETULACEAE;

EID: 0030600174     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00897-0     Document Type: Article

References (17)

1. 1. Oppolzer, W. Angew. Chem. Int. Ed. Engl., 1984, 23, 876.
2. 2. Barbachyn, M. R.: Johnson, C. R. in "Asymmetric Synthesis" Morrison, J. D.; Ed.; Academic press: New York, 1984, Vol. 3. Chap. 7.
3. 3. For a general review of sulfur directing olefins in cycloaddition please see: De Lucchi, O.; Pasquato, L. Tetrahedron, 1988, 44, 6755-6794.
4. 4. For chiral sulfinyl acrylates please see: Yang, T.-K.; Chen, C.-J.; Lee, D.-S.; Jong, T.-T.; Jiang, Y.-Z.; Mi, A.-Q. Tetrahedron: Asymmetry, 1996, 7, 57, and references cited therein.
5. 5. For oxygen directing chiral dienes in cycloaddition please see: Tripathy, R.; Carroll, P. J.; Thornton, E. R. J. Am. Chem. Soc. 1991, 113, 7630, and references cited therein.
6. 6. For nitrogen directing chiral dienes in cycloaddition please see: Murphy, J. P., and et. al. Tetrahedron Letters, 1995, 36, 9533, and references cited therein.
7. 7. For sulfur directing chiral dienes in cycloaddition please see: (a) Gosselin, P.; Bonfand, E.; Hayes, P.; Retoux, R.; Maignan, C. Tetrahedron: Asymmetry, 1994, 5, 781.
8. (b) Aversa, M. C.; Bonaccorsi, P.; Giannetto, P. Tetrahedron: Asymmetry, 1994, 5, 805.
9. (c) Arce, E.; Carmen Carreno, M.; Belen Cid. M.; Garcia Ruano, J. L. J. Org. Chem. 1994, 59, 3421, and references cited therein.
10. 8. (a) Chou, T.-S.: Tso, H.-H. Org. Prep. Proc. Int., 1989, 21, 257.
11. (b) Chou, T.-S.; Chang, C.-Y.; Wu, M.-C.; Hung, S.-H.; Liu, H.-M.; Yeh, W.-Y. J. Chem. Soc., Chem. Commun., 1992, 1643.
12. 9. Lee, D.-S.; Hung, S.-M.; Lai, M.-C.; Chu, H.-Y.; Yang, T.-K. Org. Prep. Proc. Int., 1993, 25, 673.
13. 10. Yang, T.-K.; et al. J. Org. Chem., 1994, 59, 914.
14. 11. Fujita, M.; Ishida, M.; Manako, K.; Sato, K.; Ogura, K. Tetrahedron Letters, 1993, 34, 645, and references cited therein.
15. 12. The C-4 hydrogen atoms for 6SR form cycloadducts were in the shielding cone of the imido carbonyl group, thus the chemical shifts of C-4 hydrogen for 6aRS and 6bRS were observed at δ 1.44 and 1.43 while the corresponding hydrogen in 6aSR and 6bSR resonated at δ 1.17 and 1.19, respectively.
16. 3) 6aRS: δ 11.22, 20.30, 20.90, 21.85, 24.96, 27.76, 32.80, 38.41, 38.69, 47.21, 48.76, 50.15, 71.45, 79.88, 125.62, 128.62, 129.00, 131.59, 134.63, 142.09, 177.61, 178,14. 6aSR: δ 11.19, 20.19, 20.82, 21.64, 24.35, 28.36, 32.84, 38.79, 38.97, 47.08, 49.08, 50.04, 73.00, 79.47, 126.45, 128.57, 129.03, 131.70, 134.54, 142.83, 177.31, 177.92. 6bRS: δ 11.49, 20.13, 20.51, 21.52, 24.18, 26.66, 28.50, 30.83, 32.47, 32.66, 38.72, 38.84, 46.81, 49.79, 50.93, 74.96, 84.01, 87.25, 126.48, 128.55, 129.01, 131.73, 133.10, 144.28, 177.20, 177.97. 6bSR: δ 11.36, 20.19, 20.51, 21.61, 24.79, 26.58, 27.83, 32.32, 32.39, 38.49, 38.61, 46.76, 49.26, 50.96, 72.69, 83.91, 87.24, 125.89, 128.48, 128.90, 131.61, 133.48, 143.41, 177.58, 178.15.
17. 14. Adams, H.: Neville Jones, D.; Aversa, M. C.; Bonaccorsi, P.; Giannetto, P. Tetrahedron Letters, 1993, 34, 6481.