A catalytic carbon-phosphorus ylide reaction: Phosphane-catalyzed annulation of allylic compounds with electron-deficient alkenes

Angewandte Chemie - International Edition

Volumn 42, Issue 9, 2003, Pages 1035-1037

  Du, Yishu ^a   Lu, Xiyan ^a   Zhang, Chunming ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Alkenes; Annulation; Homogeneous catalysis; Phosphanes; Ylides

Indexed keywords

CARBON; CARBONATES; CATALYSIS; OLEFINS; PHOSPHORUS;

CYCLOPENTENES;

CATALYST ACTIVITY;

ACETIC ACID; ALKENE DERIVATIVE; ALLYL COMPOUND; BROMIDE; CARBON; CARBONIC ACID DERIVATIVE; CYCLOPENTENE DERIVATIVE; PHOSPHORUS DERIVATIVE;

ARTICLE; CATALYSIS; ELECTRON;

EID: 0037416417     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200390266     Document Type: Article

References (40)

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35. 1H COSY spectra of compounds 6, 8a, 9a, and 11a are available in the Supporting Information.
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37. The isolation of the same product 3b starting from 4b and 12b implies that the reaction of 12b was initiated by the nucleophilic addition of PPh3 to the electron-deficient double bond of 12b followed by elimination of the acetate ion (compare entries 3 and 13 of Table 1). The ylide formed from the resulting phosphonium salt is the same as that generated from the reaction of 4b with PPh3. For a similar addition-elimination reaction, see: M. Harre, P. Raddatz, R. Walenta, E. Winterfeldt, Angew. Chem. 1982, 94, 496; Angew. Chem. Int. Ed. Engl. 1982, 21, 480; D. Seebach, M. Missbach, G. Calderari, M. Eberle, J. Am. Chem. Soc. 1990, 112, 7625.
38. The isolation of the same product 3b starting from 4b and 12b implies that the reaction of 12b was initiated by the nucleophilic addition of PPh3 to the electron-deficient double bond of 12b followed by elimination of the acetate ion (compare entries 3 and 13 of Table 1). The ylide formed from the resulting phosphonium salt is the same as that generated from the reaction of 4b with PPh3. For a similar addition-elimination reaction, see: M. Harre, P. Raddatz, R. Walenta, E. Winterfeldt, Angew. Chem. 1982, 94, 496; Angew. Chem. Int. Ed. Engl. 1982, 21, 480; D. Seebach, M. Missbach, G. Calderari, M. Eberle, J. Am. Chem. Soc. 1990, 112, 7625.
39. The isolation of the same product 3b starting from 4b and 12b implies that the reaction of 12b was initiated by the nucleophilic addition of PPh3 to the electron-deficient double bond of 12b followed by elimination of the acetate ion (compare entries 3 and 13 of Table 1). The ylide formed from the resulting phosphonium salt is the same as that generated from the reaction of 4b with PPh3. For a similar addition-elimination reaction, see: M. Harre, P. Raddatz, R. Walenta, E. Winterfeldt, Angew. Chem. 1982, 94, 496; Angew. Chem. Int. Ed. Engl. 1982, 21, 480; D. Seebach, M. Missbach, G. Calderari, M. Eberle, J. Am. Chem. Soc. 1990, 112, 7625.
40. In general, it is very difficult to generate the ylide directly from allylic acetate without the assistance of a transition metal. For an example of the transition-metal-assisted formation of ylide from allylic acetate, see: R. Tamura, M. Kato, K. Saegusa, M. Kakihana, D. Oda, J. Org. Chem. 1987, 52, 4121.