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Volumn 16, Issue 2, 2010, Pages 703-708

A new zincate-mediated rearrangement reaction of 2-(1-hydroxyalkyl)-1- alkylcyclopropanol

Author keywords

Cyclopropanol; Homogeneous catalysis; Organozinc ate complexes; Rearrangement; Zinc

Indexed keywords

ATE COMPLEX; CATALYTIC AMOUNTS; CYCLIC SUBSTRATES; CYCLOPROPANOL; HOMOGENEOUS CATALYSIS; ORGANOZINC ATE COMPLEXES; PENTADECANE; REARRANGEMENT REACTIONS; RING SIZES;

EID: 75649100881     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901054     Document Type: Article
Times cited : (15)

References (65)
  • 42
    • 18744363278 scopus 로고    scopus 로고
    • Treatment of an α,β-unsaturated ketone with an aldehyde in the presence of chromium(II) gives 2-(1-hydroxyalkyl)-1-alkylcyclopropanol. Meanwhile, the same reaction with the addition of chlorotrimethylsilane affords cross-pinacol coupling product. See: a) K. Takai, R. Morita, C. Toratsu, Angew. Chem. 2001, 113, 1150;
    • (2001) Angew. Chem. , vol.113 , pp. 1150
    • Takai, K.1    Morita, R.2    Toratsu, C.3
  • 45
    • 33847798461 scopus 로고
    • Still and Macdonald have reported that α-alkoxyallyl carbanions undergo preferential protonation and alkylation at the unsubstituted terminus and react with carbonyl compounds at lhe alkoxy-substituted terminus. See. W. C. Still. T. L. Macdonald. J. Org. Chem. 1976, 41, 3620.
    • (1976) J. Org. Chem. , vol.41 , pp. 3620
    • Still, W.C.1    Macdonald, T.L.2
  • 54
    • 75649115832 scopus 로고    scopus 로고
    • The react IR measurement was conducted every 30 s. Figure 1 shows the absorption intensity of 3b and 5b plotted every 30 min to simplify the figure. See the Supporting Information for more details.
    • The react IR measurement was conducted every 30 s. Figure 1 shows the absorption intensity of 3b and 5b plotted every 30 min to simplify the figure. See the Supporting Information for more details.
  • 55
    • 75649085006 scopus 로고    scopus 로고
    • Although 31 was used as a single diastereomer form, we could not determine the relative stereochemistry of 3i.
    • Although 31 was used as a single diastereomer form, we could not determine the relative stereochemistry of 3i.
  • 64
    • 75649151291 scopus 로고    scopus 로고
    • Although we attempted to trap D and E with allyl bromide and methyl iodide, the corresponding β-allylated ketone or β-methylated ketone was not obtained.
    • Although we attempted to trap D and E with allyl bromide and methyl iodide, the corresponding β-allylated ketone or β-methylated ketone was not obtained.
  • 65
    • 0033553109 scopus 로고    scopus 로고
    • 2). The reaction directly affords o-zincated aromatic compounds. This reactivity is in contrast to the low basicity found for conventional zinc reagents. Because the ligand on the zinc atom of the zincate has stronger basicity than that on conventional zinc reagents, we are expecting that a ligand of zincate complex, such as an alkoxy group, has an ability as electron donor. See: Y. Kondo. M. Shilai, M. Uchiyama, T. Sakamoto. J. Am. Chem. Soc. 1999, 121, 3539.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 3539
    • Kondo, Y.1    Shilai, M.2    Uchiyama, M.3    Sakamoto, T.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.