Asymmetric Diels-Alder Reaction of α-Sulfinylacrylate Derived from (1R, 2S, 3R)-3-Mercaptocamphan-2-ol

Tetrahedron Asymmetry

Volumn 7, Issue 1, 1996, Pages 57-60

  Yang, Teng Kuei ^a   Chen, Ching Jung ^a   Lee, Dong Sheng ^a,b   Jong, Ting Ting ^a   Jiang, Yao Zhong ^b   Mi, Ai Qiao ^b  

^a NATIONAL CHUNG HSING UNIVERSITY   (Taiwan)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

SULFINIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030043862     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(95)00420-3     Document Type: Article

References (22)

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13. (h) Alonso, I.: Belen Cid, M.: Carlos Carretero, J.; Garcia Ruano, J. L.; Hoyos, M. A. Tetrahedron :Asymmetry. 1991, 2, 1193.
14. (i) Carretero, J. C.; Garcia Ruano, J. L.; Lorente, A.; Yuste, F. Tetrahedron :Asymetry, 1993, 4, 777.
15. (a) Arai, Y.; Kuwayama, S.-i.; Takeuchi, Y.; Koizumi, T. Tetrahedron Letters. 1985, 26, 6205.
16. (b) Yang, T.-K.; Teng, T.-F.; Lee, D.-S. J. Chin. Chem. Soc. 1991, 38, 375 and 401.
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18. Yang, T.-K.; Hung, S.-M.; Chen, C.-Z.; Jiang, Y.-Z.; Mi. A.-Q. Youji Hauxue, 1993, 13, 183.
19. For a similar inducing effect of the 2-hydroxy group in the oxidation, please see: Yang, T.-K.; Chen, R.-Y.; Lee. D.-S.; Perng. W.-S.; Jiang. Y.-Z.; Mi, A.-Q.; Jong, T.-T. J. Org. Chem., 1994, 59, 914.
20. The X-ray crystallographic studies of the cycloadducts of endo-(Re)-6a and exo-(Si)-9a supported the stereochemistry that we proposed. Based on the precedent and our hypothesis, exo-(Re)-8a was the least possible product which could easily be differentiated from the highly predominated cycloadduct 7a.
21. Crystal data of endo-(Re)-6a and exo-(Si)-9a are supplied as supplementary material. The atomic coordinates have been deposited in Cambridge Cristallographic Data Centre.
22. 3) δ 11.31, 21.14, 22.31, 28.95, 32.99, 33.76, 43.99, 46.32. 47.27, 47.65. 48.41. 49.72, 52.47, 72.03, 72.99, 81.00, 133,40, 141.20, 170.28.