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Volumn 10, Issue 23, 2008, Pages 5453-5456

Sml2-promoted reformatsky-type reaction and acylation of alkyl 1-chlorocyclopropanecarboxylates

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EID: 61349192222     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8022038     Document Type: Article
Times cited : (23)

References (60)
  • 2
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    • For a recent review of Reformatsky reactions, see: b
    • For a recent review of Reformatsky reactions, see: (b) Fürstner, A. Synthesis 1989, 571.
    • (1989) Synthesis , pp. 571
    • Fürstner, A.1
  • 16
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    • 2-promoted Reformatsky-type reaction of Evans amide: (a) Fukuzawa, S.; Matsuzawa, H.; Yoshimitsu, S. J. Org. Chem. 2000, 65, 1702.
    • 2-promoted Reformatsky-type reaction of Evans amide: (a) Fukuzawa, S.; Matsuzawa, H.; Yoshimitsu, S. J. Org. Chem. 2000, 65, 1702.
  • 18
    • 2142715741 scopus 로고    scopus 로고
    • 2-promoted reactions, see: (c) Molander, G. A.; Harris, C. H. Chem. Rev. 1996, 96, 307-338.
    • 2-promoted reactions, see: (c) Molander, G. A.; Harris, C. H. Chem. Rev. 1996, 96, 307-338.
  • 26
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    • 2-promoted self-coupling of α-bromo ester in THF-HMPA: (a) Balaux, E.; Ruel, R. Tetrahedron Lett. 1996, 37, 801.
    • 2-promoted self-coupling of α-bromo ester in THF-HMPA: (a) Balaux, E.; Ruel, R. Tetrahedron Lett. 1996, 37, 801.
  • 27
    • 0028929020 scopus 로고    scopus 로고
    • 2-promoted self-Claisen condensation of α-bromo ester: (b) Park, H. S.; Lee, I. S.; Kim, Y. H. Tetrahedron Lett. 1995, 36, 1673.
    • 2-promoted self-Claisen condensation of α-bromo ester: (b) Park, H. S.; Lee, I. S.; Kim, Y. H. Tetrahedron Lett. 1995, 36, 1673.
  • 29
    • 0001320601 scopus 로고    scopus 로고
    • 2-promoted self-coupling of ketones and aldehydes, see: (a) Namy, J. L.; Souppe, J.; Kagan, H. B. Tetrahedron Lett. 1983, 24, 765.
    • 2-promoted self-coupling of ketones and aldehydes, see: (a) Namy, J. L.; Souppe, J.; Kagan, H. B. Tetrahedron Lett. 1983, 24, 765.
  • 34
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    • and references cited therein. For a recent review, see
    • For a recent review, see: Fedorynski, M. Chetn. Rev. 2003, 103, 1099, and references cited therein.
    • (2003) Chetn. Rev , vol.103 , pp. 1099
    • Fedorynski, M.1
  • 42
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    • (g) Corey, E. J.; Posner, G. H. J. Am. Chem. Soc. 1967, 89, 3911; 1968, 90, 5615.
  • 47
    • 61349118512 scopus 로고    scopus 로고
    • 3-carbon of methyl α-chloro isobutyrate. The stereocongestion around the newly formed C-C bond of 2 is less than that of acyclic α,α-dimethyl β-hydroxy ester because of the strained angle of the cyclopropane ring.
    • 3-carbon of methyl α-chloro isobutyrate. The stereocongestion around the newly formed C-C bond of 2 is less than that of acyclic α,α-dimethyl β-hydroxy ester because of the strained angle of the cyclopropane ring.
  • 50
    • 33845280057 scopus 로고
    • For a similar reaction of siloxy-substituted derivatives, see: f
    • For a similar reaction of siloxy-substituted derivatives, see: (f) Bruckner, C.; Reissig, H.-U. J. Org. Chem. 1988, 53, 2440.
    • (1988) J. Org. Chem , vol.53 , pp. 2440
    • Bruckner, C.1    Reissig, H.-U.2
  • 51
  • 52
    • 0037414487 scopus 로고    scopus 로고
    • The relative structure of 2/3 (re-face-add/si-face-add) was assigned on the basis of the typical selectivity of SmI2-promoted Reformatsky reaction (see ref 3) and Shuto's report of highly stereoselective reduction of trans-substituted cyclopropanes; see: Kazuta, Y, Abe, H, Yamamoto, T, Matsuda, A, Shuto, S. J. Org. Chem. 2003, 68, 3511
    • 2-promoted Reformatsky reaction (see ref 3) and Shuto's report of highly stereoselective reduction of trans-substituted cyclopropanes; see: Kazuta, Y.; Abe, H.; Yamamoto, T.; Matsuda, A.; Shuto, S. J. Org. Chem. 2003, 68, 3511.
  • 53
    • 61349130552 scopus 로고    scopus 로고
    • For discussion of the retro-aldol reaction, see: a, 5th ed, Smith, M. B, March, J, Eds, Wiley-Interscience: New York
    • For discussion of the retro-aldol reaction, see: (a) March's Advanced Organic Chemistry, 5th ed.; Smith, M. B., March, J., Eds.; Wiley-Interscience: New York, 2001; p 1220.
    • (2001) March's Advanced Organic Chemistry , pp. 1220
  • 57
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    • In contrast, in the similar treatment of 2h with NaH, a retro-aldol reaction occurred to give methyl bicyclo[4.1.0]heptane-7-carboxylate in 87% yield.
    • In contrast, in the similar treatment of 2h with NaH, a retro-aldol reaction occurred to give methyl bicyclo[4.1.0]heptane-7-carboxylate in 87% yield.
  • 60
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    • For a discussion of the pyramidal enolate of cyclopropanecarboxylate, see: c
    • For a discussion of the pyramidal enolate of cyclopropanecarboxylate, see: (c) Reissig, H.-U.; Böhm, I. J. Am. Chem. Soc. 1982, 104, 1735.
    • (1982) J. Am. Chem. Soc , vol.104 , pp. 1735
    • Reissig, H.-U.1    Böhm, I.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.