Application of Allenylsilanes in [3 + 2] Annulation Approaches to Oxygen and Nitrogen Heterocycles

Journal of the American Chemical Society

Volumn 107, Issue 24, 1985, Pages 7233-7235

  Danheiser, Rick L ^a   Kwasigroch, Carrie A ^a   Tsai, Yeun Min ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001006816     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00310a109     Document Type: Article

References (12)

1. (a) Danheiser, R. L.; Carini, D. J.; Basak, A. J. Am. Chem. Soc. 1981, 103, 1604. (b) Danheiser, R. L.; Carini, D. J.; Fink, D. M.; Basak, A. Tetrahedron 1983, 39, 935. (c) Danheiser, R. L.; Fink, D. M. Tetrahedron Lett. 1985, 26, 2513.
2. Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925.
3. For examples of the addition of allylsilanes to N-acyl iminium ions, see: (a) Hart, D. J.; Tsai, Y.-M. Tetrahedron Lett. 1981, 22, 1567. (b) Kraus, G. A.; Neuenschwander, K. J. Chem. Soc., Chem. Commun. 1982, 134. (c) Aratani, M.; Sawada, K.; Hashimoto, M. Tetrahedron Lett. 1982, 23, 3921. (d) Prasad, K.; Adlgasser, K.; Sharma, R.; Stutz, P. Heterocycles 1982,19, 2099. (e) Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1983, 24, 1407. (f) Hiemstra, H.; Fortgens, H. P.; Speckamp, W. N. J. Chem. Soc. 1984, 25, 3115. (g) Hiemstra, H.; Klaver, W. J.; Moolenaar, M. J.; Speckamp, W. N. J. Chem. Soc. 1984, 25, 5453. (h) Hiemstra, H.; Klaver, W. J.; Speckamp, W. N. J. Org. Chem. 1984, 49, 1149. (i) Kozikowski, A. P.; Park, P. J. Chem. Soc. 1984, 49, 1674. (j) Gramain, J. C.; Remuson, R. Tetrahedron Lett. 1985, 26, 327.
4. Westmijze, H.; Vermeer, P. Synthesis 1979, 390.
5. Partial hydrolysis of the products occurred when aqueous quenching procedures were employed.
6. Recently 3,4-dihydrofurans have been isolated as byproducts from the reaction of propargyltrimethylsilanes with acetals: Pornet, J.; Miginiac, L.; Jaworski, K.; Randrianoelina, B. Organometallics 1985, 4, 333.
7. Thus far annulations employing ketones as heteroallenophiles have been less successful. For example, reaction of the allenylsilane 4 with cyclohexanone produces the expected 2,3-dihydrofuran in only 20-25% yield.
8. 12
9. (a) Yamamoto, Y.; Yatagai, H.; Naruta, Y.; Maruyama, K. J. Am. Chem. Soc. 1980, 102, 7107. (b) Hayashi, T.; Kabeta, K.; Hamachi, I.; Kumada, M. Tetrahedron Lett. 1983, 28, 2865. (c) Denmark, S.; Weber, E. J. Helv. Chim. Acta 1983, 66, 1655.
10. 4-promoted addition of 3-substituted allenyltrimethylsilanes to aldehydes produces (mainly) syn-homopropargylic alcohols; the stereochemistry of these products was established by conversion to known compounds: Danheiser, R. L.; Carini, D. J.; Kwasigroch, C. A., unpublished results.
11. 2.
12. For examples of the related addition of allylsilanes to chiral a-alkoxy aldehydes, see: (a) Reetz, M. T.; Kesseler, K.; Schmidtberger, S.; Wenderoth, B.; Steinbach, R. Angew. Chem., Int. Ed. Engl. 1983, 22, 989. (b) Heathcock, C. H.; Kiyooka, S.-I.; Blumenkopf, T. A. J. Org. Chem. 1984, 49, 4214. (c) Reetz, M. T.; Kesseler, K.; Jung, A. Tetrahedron Lett. 1984, 25, 729. (d) For a general review of addition reactions of chiral a- and β-alkoxy carbonyl compounds, see: Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1984, 23, 556.