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Volumn 5, Issue 12, 2003, Pages 2173-2176

New stereoselective β-C-glycosidation by uncatalyzed 1,4-addition of organolithium reagents to a glycal-derived vinyl oxirane

Author keywords

[No Author keywords available]

Indexed keywords

1,2 EPOXY 3 BUTENE; EPOXIDE; GLYCOSIDE; MESYLIC ACID DERIVATIVE; ORGANOLITHIUM COMPOUND; ORGANOMETALLIC COMPOUND;

EID: 0141630549     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034662f     Document Type: Article
Times cited : (38)

References (40)
  • 29
    • 0141441539 scopus 로고    scopus 로고
    • note
    • In the present context, the 6-O-trityl group of the previous epoxide 1 was replaced with the benzyl group because of the greater stability of the latter to a wide range of reaction conditions.
  • 30
    • 0141664552 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum a few minutes after the addition of the base.
  • 32
    • 0141553072 scopus 로고    scopus 로고
    • note
    • Less than 5% of the corresponding anti 1,2-addition products were present in some cases. Products from an α-1,4 addition process were not observed at all.
  • 33
    • 0141664551 scopus 로고    scopus 로고
    • note
    • Under protocol B, it was hoped that the organometallic reagents might behave as a base and thereby promote epoxide formation from hydroxy mesylate 3 and then undergo an addition reaction.
  • 34
    • 0141664553 scopus 로고    scopus 로고
    • note
    • This observation indicates that alkyllithium and PhLi do not behave, in the present case, as a base, which is necessary for the cyclization of hydroxy mesylate 3 to epoxide 4.
  • 35
    • 0141664554 scopus 로고    scopus 로고
    • note
    • The only exception is given by the β-methyl derivative 10β [δ C(5) = 73.79 ppm]. However, the β-C-glycosidic configuration for this compound was firmly established by corresponding NOE experiment.
  • 37
    • 0141664555 scopus 로고    scopus 로고
    • note
    • From t-BuOK used for the cyclization of 3 to epoxide 4.
  • 38
    • 0141776420 scopus 로고    scopus 로고
    • note
    • As suggested by a Rewiever, epoxide 4 is not a necessary intermediate for the generation of 16 and 17, via protocol B. A Grob fragmentation process on hydroxy mesylate 3 could lead directly to the observed products.
  • 39
    • 0001312924 scopus 로고
    • Trost, B. M., Fleming, I., Pattenden, G., Eds.; Pergamon: Oxford
    • Rickborn, B. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Pattenden, G., Eds.; Pergamon: Oxford, 1991; Vol 3, pp 733-775.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 733-775
    • Rickborn, B.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.