Radical Hydrostannylation, Pd(0)-Catalyzed Hydrostannylation, Stannylcupration of Propargyl Alcohols and Enynols: Regio- and Stereoselectivities

Journal of Organic Chemistry

Volumn 62, Issue 22, 1997, Pages 7768-7780

  Betzer, Jean François ^a   Delaloge, Francette ^a   Muller, Benoît ^a   Pancrazi, Ange ^a   Prunet, Joëlle ^a  

^a LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001422640     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9710339     Document Type: Article

References (54)

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48. A secondary effect was observed in this reaction: for example reaction of propargyl alcohol I (PG = H) led to a 55:45 ratio of proximal/ distal tin derivative and a 91:9 ratio when the hydroxyl function was protected (PG = Ph). A stabilizing complex A between palladium and the alcohol substituent could be involved to explain this observed regioselectivity.
49. When (Z)-enynol IX was protected as a TBS ether, Pd(0)-catalyzed hydrostannylation gave also the pure proximal corresponding dienylstannane in 54% yield (45% starting material recovered). Surprisingly enynol (E)-VII also protected as a TBS derivative gave the proximal isomer in only 14% yield and the (E)-3-methyl-[(tert-butyldimethylsilyl)oxy]-2,4-pentadiene in 56% yield as well.
50. 3SnCl to the cuprate solution. When the reaction was run in presence of methanol, less than 1% of the distannyl deivative 22c was obtained whereas without methanol, 22c was isolated in 61% yield.
51. cis-Bis-vinylstannanes were also obtained via other methods by Oehlschlager, A. C (ref 11) and Piers, E.; Tillyer R. D. Can. J. Chem. 1996, 74, 2048. These latter authors in the same paper, as well as Lambert, M.-P.; Ratier, M.; Duboudin, J.-G., Pétraud, N. J. Organomet. Chem. 1994, 467, 181, also described the preparation of trans-bisvinylstannanes.
52. cis-Bis-vinylstannanes were also obtained via other methods by Oehlschlager, A. C (ref 11) and Piers, E.; Tillyer R. D. Can. J. Chem. 1996, 74, 2048. These latter authors in the same paper, as well as Lambert, M.-P.; Ratier, M.; Duboudin, J.-G., Pétraud, N. J. Organomet. Chem. 1994, 467, 181, also described the preparation of trans-bisvinylstannanes.
53. Kochi, J. K. Organometallic Mechanisms and Catalysis, Academic Press, New York, 1978.
54. In both cases described below, stannylcupration led to the corresponding bis-stannanes as the major products in 44% and 28% yield. The monovinylstannane was isolated in each case in 8-10% yield.