Stereoselective synthesis of cyclopropanes via homoallylic participation

Bulletin of the Chemical Society of Japan

Volumn 69, Issue 1, 1996, Pages 31-39

  Nagasawa, Tetsuya ^a   Handa, Yasuhiko ^a   Onoguchi, Yuka ^a   Suzuki, Keisuke ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE; ICOSANOID;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030061066     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.69.31     Document Type: Article

References (47)

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6. For preliminary accounts of the results, see: a) T. Nagasawa, Y. Handa, Y. Onoguchi, S. Ohba, and K. Suzuki, Synlett, 1995, 739; b) T. Nagasawa, Y. Onoguchi, T. Matsumoto, and K. Suzuki, Synlett, 1995, 1023.
7. For preliminary accounts of the results, see: a) T. Nagasawa, Y. Handa, Y. Onoguchi, S. Ohba, and K. Suzuki, Synlett, 1995, 739; b) T. Nagasawa, Y. Onoguchi, T. Matsumoto, and K. Suzuki, Synlett, 1995, 1023.
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29. 10a) Mono-methylated one 41 underwent the cyclization-methylation to give the isopropyl substituted product 42 in high yield. Bis-methylated one 43 underwent methylation to give t-butyl substituted cyclopropane 44 in high yield as a sole diastereomer.
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31. It would be interesting to catalogue this reaction as an ionic version of group-transfer cyclization, 5′→6′; For atom/group transfer cyclization of radical species, see: C. P. Jasperse, D. P. Curran, and T. L. Fevig, Chem. Rev., 91, 1237 (1991).
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