Stereoselective construction of functionalized, trisubstituted (Z)-allylsilanes and (Z)-iodoalkenes

Synthetic Communications

Volumn 26, Issue 3, 1996, Pages 433-444

  Fish, Paul V ^a,b  

^a STANFORD UNIVERSITY   (United States)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ORGANOIODINE DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030028576     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919608003634     Document Type: Article

References (20)

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2. (a) Brady, S. F.; Ilton, M. A.; Johnson, W. S. J. Am. Chem. Soc. 1968, 90, 2882.
3. (b) Johnson, W. S.; Werthemann, L.; Bartlett, W. R.; Brocksom, T. J.; Li, T. -t.; Faulkner, D. J.; Petersen, M. R. J. Am. Chem. Soc. 1970, 92, 741.
4. Fish, P. V.; Reddy, P. S.; Lee, C. H.; Johnson, W. S. Tetrahedron Lett. 1992, 33, 8001.
5. These methods are compatible with polyene synthesis. For a recent example, see: Fish, P. V.; Johnson, W. S. J. Org. Chem. 1994, 59, 2324 and references therein.
6. Methods of allylsilane formation: (a) Fleming, I. "Allylsilanes, Allylstannanes and Related Systems." In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 563-593. (b) Sarkar, T. M. Synthesis 1990, 969; 1101. (c) Fleming, I.; Dunogues, J.; Smithers, R. Organic Reactions 1989, 37, 57-575.
7. Methods of allylsilane formation: (a) Fleming, I. "Allylsilanes, Allylstannanes and Related Systems." In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 563-593. (b) Sarkar, T. M. Synthesis 1990, 969; 1101. (c) Fleming, I.; Dunogues, J.; Smithers, R. Organic Reactions 1989, 37, 57-575.
8. Methods of allylsilane formation: (a) Fleming, I. "Allylsilanes, Allylstannanes and Related Systems." In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 563-593. (b) Sarkar, T. M. Synthesis 1990, 969; 1101. (c) Fleming, I.; Dunogues, J.; Smithers, R. Organic Reactions 1989, 37, 57-575.
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11. For an example of the 1,5-migration of silicon from carbon to oxygen of a γ-silyl α,β-unsaturated ketone, see: Casey, C. P.; Jones, C. R.; Tukada, H. J.Org. Chem. 1981, 46, 2089. Note, γ-silyl α,β-unsaturated esters (e.g. 4) are thermally stable and do not undergo this rearrangement,
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19. (b) Zweifel, G.; Nagase, K.; Brown, H. C. J. Am. Chem. Soc. 1962, 84, 190.
20. Correspondence regarding this Article should be addressed to W. S. Johnson, Stanford University.