Oxidation of 3-Tributylstannyl-1-alkenyl carbamates with Selenium Dioxide

Synlett

Volumn 1996, Issue 9, 1996, Pages 867-870

  Madec, David ^a   Férézou, Jean Pierre ^a  

^a LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542395730     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5597     Document Type: Article

References (37)

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3. Marshall, J. A. Chem. Rev. 1996, 96, 31.
4. For pioneering work on the use of 1-substituted 3-stannylated alkenyl carbamates, see: Krämer, T.; Schwark, J.-R.; Hoppe, D.; Zschage, O. Tetrahedron Lett. 1989, 30, 7037; Zschage, O.; Schwark, J.-R.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1989, 29, 296; Hoppe, D.; Krämer, T.; Schwark, J.-R.; Zschage, O. Pure Appl. Chem. 1990, 62, 1999. For utilization of enantiomerically enriched 3-stannylated alkenyl carbamates in acid catalysed sterocontrolled homoaldol reactions, see: Paulsen, H.; Graeve, C.; Hoppe, D. Synthesis 1996, 141.
5. For pioneering work on the use of 1-substituted 3-stannylated alkenyl carbamates, see: Krämer, T.; Schwark, J.-R.; Hoppe, D.; Zschage, O. Tetrahedron Lett. 1989, 30, 7037; Zschage, O.; Schwark, J.-R.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1989, 29, 296; Hoppe, D.; Krämer, T.; Schwark, J.-R.; Zschage, O. Pure Appl. Chem. 1990, 62, 1999. For utilization of enantiomerically enriched 3-stannylated alkenyl carbamates in acid catalysed sterocontrolled homoaldol reactions, see: Paulsen, H.; Graeve, C.; Hoppe, D. Synthesis 1996, 141.
6. For pioneering work on the use of 1-substituted 3-stannylated alkenyl carbamates, see: Krämer, T.; Schwark, J.-R.; Hoppe, D.; Zschage, O. Tetrahedron Lett. 1989, 30, 7037; Zschage, O.; Schwark, J.-R.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1989, 29, 296; Hoppe, D.; Krämer, T.; Schwark, J.-R.; Zschage, O. Pure Appl. Chem. 1990, 62, 1999. For utilization of enantiomerically enriched 3-stannylated alkenyl carbamates in acid catalysed sterocontrolled homoaldol reactions, see: Paulsen, H.; Graeve, C.; Hoppe, D. Synthesis 1996, 141.
7. For pioneering work on the use of 1-substituted 3-stannylated alkenyl carbamates, see: Krämer, T.; Schwark, J.-R.; Hoppe, D.; Zschage, O. Tetrahedron Lett. 1989, 30, 7037; Zschage, O.; Schwark, J.-R.; Hoppe, D. Angew. Chem., Int. Ed. Engl. 1989, 29, 296; Hoppe, D.; Krämer, T.; Schwark, J.-R.; Zschage, O. Pure Appl. Chem. 1990, 62, 1999. For utilization of enantiomerically enriched 3-stannylated alkenyl carbamates in acid catalysed sterocontrolled homoaldol reactions, see: Paulsen, H.; Graeve, C.; Hoppe, D. Synthesis 1996, 141.
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15. 2/pyridine mixture in the case of substrates bearing acid labile groups, Camps, F.; Coll, J.; Parente, A. Synthesis, 1978, 215.
16. See for significant examples: a) Arylseleninic acids obtained from diselenide and t-butyl hydroperoxide, Hori, T.; Sharpless, K. B. J. Org. Chem. 1978, 43, 1689. b) 2-Pyridineseleninic anhydride, Crich, D.; Barton, D. H. R. Tetrahedron, 1985, 41, 4359.
17. See for significant examples: a) Arylseleninic acids obtained from diselenide and t-butyl hydroperoxide, Hori, T.; Sharpless, K. B. J. Org. Chem. 1978, 43, 1689. b) 2-Pyridineseleninic anhydride, Crich, D.; Barton, D. H. R. Tetrahedron, 1985, 41, 4359.
18. c) Pentafluorobenzeneseleninic acid and 2-(N-oxido)pyridineseleninic anhydride, Barton, D. H. R.; Wang, T. -L. Tetrahedron Lett. 1994, 35, 5149.
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21. For a review see: Kitching, W. Oxidation of Carbon-Metal Bonds, in Comprehensive Organic Synthesis; Trost, B. M. and Fleming, I. Eds; Pergamon Press: Oxford, 1991; 7, 613 and references cited therein. A new example involves oxidative clivage of stannanes with ozone: Linderman, R. J.; Jaber, M. Tetrahedron Lett. 1994, 35, 5993.
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27. The preparation of the (E)-3b has been carried out from (E)-crotonaldehyde as following: (Equation Presented) 93-99% For related transformations, see: Sengupta, S.; Snieckus, V. J. Org. Chem. 1990, 55, 5680. Marshall, J. A.; Welmaker, G. S. J. Org. Chem. 1992, 57, 7158.
28. The preparation of the (E)-3b has been carried out from (E)-crotonaldehyde as following: (Equation Presented) 93-99% For related transformations, see: Sengupta, S.; Snieckus, V. J. Org. Chem. 1990, 55, 5680. Marshall, J. A.; Welmaker, G. S. J. Org. Chem. 1992, 57, 7158.
29. a) Madec, D.; Pujol, S.; Henryon, V.; Férézou J. P. Synlett 1995, 435.
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32. 3 solution. After decantation the aqueous phase was extracted with 3×10 ml of diethyl ether. The combined organic phases were treated as above to give, after flash chromatography, pure alcohol 4a (207 mg, 98% yield, E/Z = 95:5).
33. Camps, F.; Coll, J.; Parente, A. Synthesis 1978, 215.
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35. As claimed by one referee, the weaker C-Sn than C-H bond can also facilitate the initiation of the reaction.
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