Nucleophilic additions to a spiro[2,4]hepta-4,6-diene 4-nitrile: Synthesis of 1,2-disubstituted cyclopentenes

Tetrahedron Letters

Volumn 39, Issue 32, 1998, Pages 5675-5678

  Starr, Jeremy T ^a   Baudat, Alain ^a   Carreira, Erick M ^a  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

Cleavage reactions; Cyclopentadienes; Cyclopentenes; Cyclopropanes

Indexed keywords

CYCLOPENTADIENE DERIVATIVE; CYCLOPENTENE DERIVATIVE; CYCLOPROPANE DERIVATIVE; SPIRO COMPOUND; SPIRO[2,4]HEPTA 4,6 DIENE 4 NITRILE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CYCLIZATION; ENANTIOMER; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032490979     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01143-5     Document Type: Article

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29. 11. Nucleophilic additions to spiro[2,4]heptadiene have been reported by Kauffmann and co-workers, see Kauffmann, T.; Ennen, J.; Lhotak, H.; Rensing, A.; Steinseifer, F.; Woltermann A. Angew. Chem., Int. Ed. Engl. 1980, 19, 328. The addition of diphenylarsenide and the 1,3-diphenyl-2-azaallyl anion to spiro[2,4]heptadiene proceeded in 68 and 87% yields, respectively; addition of other nucleophiles proceeded in 17-43% yield. See also, Kauffmann, T.; Berghus, K.; Ennen, J. Chem. Ber. 1985, 118, 3724; Eilbracht, P.; Totzauer, W. Chem. Ber. 1982, 115, 1669.
30. 11. Nucleophilic additions to spiro[2,4]heptadiene have been reported by Kauffmann and co-workers, see Kauffmann, T.; Ennen, J.; Lhotak, H.; Rensing, A.; Steinseifer, F.; Woltermann A. Angew. Chem., Int. Ed. Engl. 1980, 19, 328. The addition of diphenylarsenide and the 1,3-diphenyl-2-azaallyl anion to spiro[2,4]heptadiene proceeded in 68 and 87% yields, respectively; addition of other nucleophiles proceeded in 17-43% yield. See also, Kauffmann, T.; Berghus, K.; Ennen, J. Chem. Ber. 1985, 118, 3724; Eilbracht, P.; Totzauer, W. Chem. Ber. 1982, 115, 1669.
31. 11. Nucleophilic additions to spiro[2,4]heptadiene have been reported by Kauffmann and co-workers, see Kauffmann, T.; Ennen, J.; Lhotak, H.; Rensing, A.; Steinseifer, F.; Woltermann A. Angew. Chem., Int. Ed. Engl. 1980, 19, 328. The addition of diphenylarsenide and the 1,3-diphenyl-2-azaallyl anion to spiro[2,4]heptadiene proceeded in 68 and 87% yields, respectively; addition of other nucleophiles proceeded in 17-43% yield. See also, Kauffmann, T.; Berghus, K.; Ennen, J. Chem. Ber. 1985, 118, 3724; Eilbracht, P.; Totzauer, W. Chem. Ber. 1982, 115, 1669.
32. 12. The stereoisomeric purity was assayed by gas chromatography using a J&W CDXB column.