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Volumn 73, Issue 3, 2008, Pages 1093-1098

Zirconium-promoted epoxide rearrangement-alkynylation sequence

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRONS; FUNCTIONAL GROUPS; SULFUR COMPOUNDS; SYNTHESIS (CHEMICAL); ZIRCONIUM COMPOUNDS;

EID: 38849090733     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702306k     Document Type: Article
Times cited : (24)

References (56)
  • 29
    • 0037204712 scopus 로고    scopus 로고
    • Molander, G. A.; St. Jean, J.; D. J. J. Org. Chem. 2002, 67, 3861-3865.
    • (e) Molander, G. A.; St. Jean, J.; D. J. J. Org. Chem. 2002, 67, 3861-3865.
  • 39
    • 33847668813 scopus 로고    scopus 로고
    • When compound 1 on aluminum foil was hit with a hammer, there was no sign of a spark or explosive nature of 1. This material was also heated to 150°C, and we did not observe any alarming phenomena except for slow decomposition. Although more extensive studies may be needed, the silver acetylides shown in this paper were prepared multiple times without an accident. Also, we safely performed the Cp2ZrCl2/AgOTf-promoted alkynylation in the following papers on 140 mmol scale as part of the FR901464/meayamycin synthesis: Albert B. J, Sivaramakrishnan, A, Naka, T, Czaicki, N. L, Koide, K, J. Am. Chem. Soc. 2007, 129, 2648-2659;
    • 2/AgOTf-promoted alkynylation in the following papers on 140 mmol scale as part of the FR901464/meayamycin synthesis: Albert B. J.; Sivaramakrishnan, A.; Naka, T.; Czaicki, N. L.; Koide, K., J. Am. Chem. Soc. 2007, 129, 2648-2659;
  • 49
    • 38849104051 scopus 로고    scopus 로고
    • Many silver acetylides including 1 could not be used due to its poor solubility in organic solvents, but acetylide 20 was soluble in organic solvents and thus used.
    • Many silver acetylides including 1 could not be used due to its poor solubility in organic solvents, but acetylide 20 was soluble in organic solvents and thus used.
  • 51
    • 38849168532 scopus 로고    scopus 로고
    • EtOH was used instead of MeOH for the preparation of the silver acetylide 20 from 3
    • EtOH was used instead of MeOH for the preparation of the silver acetylide 20 from 3,3-diethoxypropyne.
    • 3-diethoxypropyne


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.