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Volumn 63, Issue 13, 1998, Pages 4449-4458

Stereochemical and Mechanistic Studies on Conjugate Addition of Organocuprates to Acyclic Enones and Enoates: Simple Rule for Diastereofacial Selectivity

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EID: 0000285765     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980308x     Document Type: Article
Times cited : (38)

References (91)
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    • (a) Posner, G. H. Org. React. 1972, 19, 1-113; 1975, 22, 253- 400. Posner, G. H. An Introduction to Synthesis Using Organocopper Reagents; John Wiley & Sons; New York, 1980.
    • (1972) Org. React. , vol.19 , pp. 1-113
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  • 2
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    • (a) Posner, G. H. Org. React. 1972, 19, 1-113; 1975, 22, 253- 400. Posner, G. H. An Introduction to Synthesis Using Organocopper Reagents; John Wiley & Sons; New York, 1980.
    • (1975) Org. React. , vol.22 , pp. 253-400
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    • (f) Lipshutz, B. H. Synthesis 1987, 325-341; Synlett 1990, 119-128.
    • (1987) Synthesis , pp. 325-341
    • Lipshutz, B.H.1
  • 9
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    • (f) Lipshutz, B. H. Synthesis 1987, 325-341; Synlett 1990, 119-128.
    • (1990) Synlett , pp. 119-128
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    • (b) Yamamoto, Y.; Nishii, S.; Ibuka, T. J. Chem. Soc., Chem. Commun. 1987, 464-466, 1572-1573; J. Am. Chem. Soc. 1988, 110, 617-618.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 617-618
  • 50
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    • note
    • 5a,d
  • 51
    • 85034471786 scopus 로고    scopus 로고
    • note
    • 1H NMR in the extracts after workup.
  • 52
    • 85034474781 scopus 로고    scopus 로고
    • note
    • The configuration at C(22) of the conjugate addition products (23, 24, 27, and 28) was assigned by analogy with the facial selectivity of the cuprate addition to enones 1-4. The E- and Z-geometrically isomeric pair of enoates (5-8) showed reverse facial selectivity, which was the same as that of enones 1-4, so that both the mechanism and facial selectivity of the reaction with enoates 5-8 are assumed to be the same as those of the reaction with enones 1-4.
  • 53
    • 85034467147 scopus 로고    scopus 로고
    • 2c,d
    • 2c,d
  • 54
    • 85034463435 scopus 로고    scopus 로고
    • Z to E isomerization was observed in byproducts 20 and 21
    • (b) Z to E isomerization was observed in byproducts 20 and 21.
  • 60
    • 85034474987 scopus 로고    scopus 로고
    • MMX (an enhanced version of MM2) was calculated using the software PCMODEL (Serena Software, Bloomington, IN)
    • MMX (an enhanced version of MM2) was calculated using the software PCMODEL (Serena Software, Bloomington, IN).
  • 63
    • 0002451214 scopus 로고
    • Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199-2204. Anh, N. T.; Eisenstein, O. Nouv. J. Chim. 1977, 1, 61- 70.
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    • Anh, N.T.1    Eisenstein, O.2
  • 64
    • 85034486372 scopus 로고    scopus 로고
    • note
    • 6 The configurations of other cuprate addition products 15, 16, 23, 24, 27, and 28 were assigned on the basis of an assumption that those cuprate additions operate via a similar mechanism and hence have similar facial selectivity.
  • 88
    • 85034469889 scopus 로고    scopus 로고
    • note
    • 2O as the Lewis acid in place of TMSCl and HMPA gave unsatisfactory results in our studies.
  • 89
    • 85034477919 scopus 로고    scopus 로고
    • note
    • We have confirmed that this rule can be applicable to almost all known stereochemical results of cuprate additions to acyclic enones and enoates having γ-alkoxy or γ-phenyl substituants. These results will be reported separately.
  • 90
    • 85034476625 scopus 로고    scopus 로고
    • In entries 14, 15, 17, 21, 23, and 26 in Table 1, the residue was chromatographed on silica gel at this stage to isolate the byproduct 20, 21, or 22
    • In entries 14, 15, 17, 21, 23, and 26 in Table 1, the residue was chromatographed on silica gel at this stage to isolate the byproduct 20, 21, or 22.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.