Reaction of 2-(Ethoxycarbonyl)pentadienylsilane under Ritter Condition. Formation of α-Methylene-γ-lactone by Self-cyclization
作者： Chiaki Kuroda , Naoko Mitsumata
DOI: 10.1246/CL.1994.1375
关键词:
摘要: An acylative C(3)-C(4)-bond cleavage of 4,5-disubstituted-2-trimethylsilylmethylpenta-2,4-dienoate occurred by treatment with trifluoromethanesulfonic acid in nitriles, while a self-cyclization giving an α-methylene-γ-lactone also when the reactions were carried out bulky nitriles.
csj.jp参考文章(9)
Tooru Fujiwara, Koichi Morita, Takeshi Takeda, A New Method for the Preparation of α-Methylene-γ-butyrolactones Using 3-Ethoxycarbonyl-3-(phenylsulfonyl)cyclobutanone Bulletin of the Chemical Society of Japan. ,vol. 62, pp. 1524- 1527 ,(1989) , 10.1246/BCSJ.62.1524
Wayne M. Best, David A. Widdowson, Reactions related to coenzyme B12 dependent rearrangements: Metal mediated free radical acyl migrations in methyl and cyclopropyl substituted models Tetrahedron. ,vol. 45, pp. 5943- 5954 ,(1989) , 10.1016/S0040-4020(01)89121-3
Chiaki Kuroda, Shigeru Shimizu, Takahiro Haishima, James Y. Satoh, Synthesis of a Stereoisomer of Frullanolide Utilizing the Intramolecular Cyclization ofω-Formyl-2-alkenylsilane Bulletin of the Chemical Society of Japan. ,vol. 66, pp. 2298- 2303 ,(1993) , 10.1246/BCSJ.66.2298
J Pornet, B Khouz, L Miginiac, Ethoxy-1 trimethylsilyl-3 propyne-1 : synthon pour la preparation de silanes α-fonctionnels allyliques, dieniques ou trieniques conjugues. Tetrahedron Letters. ,vol. 26, pp. 1861- 1862 ,(1985) , 10.1016/S0040-4039(00)94757-9
Chiaki Kuroda, Yuki Ohnishi, James Y. Satoh, Intramolecular cyclization of β-(alkoxycarbonyl)allylsilane with conjugated ketone. A new entry to bicyclo[4.3.0]nonane Tetrahedron Letters. ,vol. 34, pp. 2613- 2616 ,(1993) , 10.1016/S0040-4039(00)77638-6
Gian Paolo Boldrini, Diego Savoia, Emilio Tagliavini, Claudio Trombini, Achille Umani-Ronchi, Active metals from potassium-graphite. Zinc-graphite-promoted synthesis of β-hydroxy esters, homoallylic alcohols, and α-methylene-γ-butyrolactones Journal of Organic Chemistry. ,vol. 48, pp. 4108- 4111 ,(1983) , 10.1021/JO00170A049
Kiyoshi Nishitani, Koji Yamakawa, A facile synthesis of bicyclic α-methylene-γ-lactones by intramolecular cyclization of allylsilylated aldehydes Tetrahedron Letters. ,vol. 28, pp. 655- 658 ,(1987) , 10.1016/S0040-4039(00)95805-2
J. Pornet, A. Rayadh, L. Miginiac, Reaction de cycloaddition entre L'ethoxy-1 trimethylsilyl-3 propyne-1 et les acetals : Synthese de carbethoxy-2 trimethylsilanes allyliques, dieniques ou enyniques diversement substitues Tetrahedron Letters. ,vol. 27, pp. 5479- 5482 ,(1986) , 10.1016/S0040-4039(00)85242-9
Barry M. Trost, [3+2] Cycloaddition Approaches to Five‐Membered Rings via Trimethylenemethane and Its Equivalents [New Synthetic Methods (55)] Angewandte Chemie. ,vol. 25, pp. 1- 20 ,(1986) , 10.1002/ANIE.198600013