1,9-Stereocontrol from 1,7-induction using an allylstannane followed by an Ireland-Claisen rearrangement

Tetrahedron

Volumn 55, Issue 12, 1999, Pages 3723-3734

  Moffatt, Ella Maria ^a   Thomas, Eric J ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; ACETOACETIC ACID; ALLYL COMPOUND; ALLYL SULFIDE; BENZALDEHYDE; ETHER; TETRAHYDROFURAN; TIN DERIVATIVE;

ACETYLATION; ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CONFORMATION; ENANTIOMER; ISOMERISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OPTICAL ROTATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIC MIXTURE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033582995     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01179-X     Document Type: Article

References (18)

1. Thomas, E. J. Chem. Commun. 1997, 411-418.
2. Carey, J. S.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1994, 283-284.
3. Dorling, K. E.; Thomas, E. J. unpublished observations.
4. Ireland, R. E.; Mueller, R. H. J. Am. Chem. Soc. 1972, 94, 5897-5898; Ireland, R. E.; Wipf, P.; Armstrong III, J. D. J. Org. Chem. 1991, 56, 650-657; Zeigler, F. E. Chem. Rev. 1988, 88, 1423-1452.
5. Ireland, R. E.; Mueller, R. H. J. Am. Chem. Soc. 1972, 94, 5897-5898; Ireland, R. E.; Wipf, P.; Armstrong III, J. D. J. Org. Chem. 1991, 56, 650-657; Zeigler, F. E. Chem. Rev. 1988, 88, 1423-1452.
6. Ireland, R. E.; Mueller, R. H. J. Am. Chem. Soc. 1972, 94, 5897-5898; Ireland, R. E.; Wipf, P.; Armstrong III, J. D. J. Org. Chem. 1991, 56, 650-657; Zeigler, F. E. Chem. Rev. 1988, 88, 1423-1452.
7. Hassanaly, P.; Dou, H. J. M.; Metzger, J.; Assef, G.; Kister, J. Synthesis 1977, 253-254.
8. Collins, L; Nadin, A.; Holmes, A. B.; Long, M. E.; Man, J.; Baker, R. J. Chem. Soc., Perkin Trans. 1 1994, 2205-2215.
9. Mitsunobu, O. Synthesis 1981, 1-28.
10. Mukaiyama, T.; Tomimori, K.; Oriyama, T. Chemistry Lett. 1985, 1359-1362.
11. Wilcox, C. S.; Babston, R. E. J. Am. Chem. Soc. 1986, 108, 6636-6642; Cha, J. K.; Lewis, S. C. Tetrahedron Lett. 1984, 25, 5263-5266; Redlich, H.; Lenfers, J. B.; Thormahlen, S. Synthesis 1992, 1112-1118.
12. Wilcox, C. S.; Babston, R. E. J. Am. Chem. Soc. 1986, 108, 6636-6642; Cha, J. K.; Lewis, S. C. Tetrahedron Lett. 1984, 25, 5263-5266; Redlich, H.; Lenfers, J. B.; Thormahlen, S. Synthesis 1992, 1112-1118.
13. Wilcox, C. S.; Babston, R. E. J. Am. Chem. Soc. 1986, 108, 6636-6642; Cha, J. K.; Lewis, S. C. Tetrahedron Lett. 1984, 25, 5263-5266; Redlich, H.; Lenfers, J. B.; Thormahlen, S. Synthesis 1992, 1112-1118.
14. Evans, D. A.; Chapman, K. T.; Bisaha, J. Am. Chem. Soc. 1988, 110, 1238-1256.
15. Qian, X.; Russell, K. C.; Boteju, L. W.; Hruby, V. J. Tetrahedron 1995, 51, 1033-1054.
16. Braun, M.; Waldmueller, D. Synthesis 1989, 11, 856-858; Braun, M.; Devant, R. Tetrahedron Lett. 1984, 25, 5031-5034.
17. Braun, M.; Waldmueller, D. Synthesis 1989, 11, 856-858; Braun, M.; Devant, R. Tetrahedron Lett. 1984, 25, 5031-5034.
18. Bulman Page, P. C.; Marchington, A. P.; Graham, L. J.; Harkin, S. A.; Wood, W. W. Tetrahedron 1993, 49, 10369-10386.