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Volumn 64, Issue 2, 1999, Pages 547-555

Cyclopropanation reactions of pyroglutamic acid-derived synthons with akylidene transfer reagents

Author keywords

[No Author keywords available]

Indexed keywords

ARGININE; CYCLOPROPANE; GLUTAMIC ACID; LACTAM DERIVATIVE; PYROGLUTAMIC ACID DERIVATIVE; REAGENT;

EID: 0033593515     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9816109     Document Type: Article
Times cited : (92)

References (37)
  • 5
    • 0025074114 scopus 로고
    • (a) For a review of cyclopropane amino acids, see: Stammer, C. H. Tetrahedron 1990, 46, 2231.
    • (1990) Tetrahedron , vol.46 , pp. 2231
    • Stammer, C.H.1
  • 9
    • 0025992651 scopus 로고
    • and references therein
    • (c) Romo, D.; Meyers, A. I. Tetrahedron 1991, 47, 9503 and references therein.
    • (1991) Tetrahedron , vol.47 , pp. 9503
    • Romo, D.1    Meyers, A.I.2
  • 15
    • 0344071488 scopus 로고    scopus 로고
    • note
    • H1-H2. See ref 2.
  • 18
    • 0344071483 scopus 로고    scopus 로고
    • Exo denotes addition to the exo face of the bicyclic lactam, whereas anti and syn denote the cyclopropane stereochemistry
    • Exo denotes addition to the exo face of the bicyclic lactam, whereas anti and syn denote the cyclopropane stereochemistry.
  • 19
    • 0344933573 scopus 로고    scopus 로고
    • note
    • The stereochemistry of the vinyl group was assigned by the presence of a positive NOE between H1 and H3 for the anti isomer and the absence of a positive NOE between H1 and H3 for the syn isomer (see Scheme 1 for numbering) or by coupling constants as described in ref 5b. All additional stereochemical assignments were accomplished in an analogous manner.
  • 25
    • 0344502769 scopus 로고    scopus 로고
    • The dimerization product is formed as a single diastereomer. We have not attempted to assign relative stereochemistry. (figure presented)
    • The dimerization product is formed as a single diastereomer. We have not attempted to assign relative stereochemistry. (figure presented)
  • 27
    • 0344071481 scopus 로고    scopus 로고
    • Although it is unusual to think of an ethyl group as smaller than a vinyl group, in this instance, a vinyl group may be considered more sterically demanding because it is coplanar with the sulfur and anionic carbon, whereas with the ethyl group, the terminal methyl may rotate away from the pyrrolidine ring
    • Although it is unusual to think of an ethyl group as smaller than a vinyl group, in this instance, a vinyl group may be considered more sterically demanding because it is coplanar with the sulfur and anionic carbon, whereas with the ethyl group, the terminal methyl may rotate away from the pyrrolidine ring.
  • 28
    • 33947485650 scopus 로고
    • A possible explanation for the lack of selectivity is that following conjugate addition disproportionation scrambles the stereochemistry at the newly formed stereocenter. Products which arise from this alternate mechanistic pathway have been reported: (a) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1963, 86, 1640. (b) Tamura, Y.; Taniguchi, H.; Miyamoto, T.; Tsunekawa, M.; Ikeda, M. J. Org. Chem. 1974, 39, 3519. (figure presented)
    • (1963) J. Am. Chem. Soc. , vol.86 , pp. 1640
    • Corey, E.J.1    Chaykovsky, M.2
  • 29
    • 0345364997 scopus 로고
    • figure presented
    • A possible explanation for the lack of selectivity is that following conjugate addition disproportionation scrambles the stereochemistry at the newly formed stereocenter. Products which arise from this alternate mechanistic pathway have been reported: (a) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1963, 86, 1640. (b) Tamura, Y.; Taniguchi, H.; Miyamoto, T.; Tsunekawa, M.; Ikeda, M. J. Org. Chem. 1974, 39, 3519. (figure presented)
    • (1974) J. Org. Chem. , vol.39 , pp. 3519
    • Tamura, Y.1    Taniguchi, H.2    Miyamoto, T.3    Tsunekawa, M.4    Ikeda, M.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.