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Volumn 26, Issue 1, 2007, Pages 30-32

Ambiphilic vinylcarbenoid reactivity of (α-(tributylstannyl)-,π- allyl)palladium(II) species

Author keywords

[No Author keywords available]

Indexed keywords

DIMERIZATION; OLEFINS; ORGANOMETALLICS; TIN COMPOUNDS;

EID: 33846263429     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0609416     Document Type: Article
Times cited : (27)

References (37)
  • 1
    • 4344566130 scopus 로고    scopus 로고
    • J Trost, B. M. J. Org. Chem. 2004, 69, 5813-5837 and references therein.
    • J Trost, B. M. J. Org. Chem. 2004, 69, 5813-5837 and references therein.
  • 20
    • 33846235224 scopus 로고    scopus 로고
    • Using 3b in DME, no trapping was observed at room temperature, and at 40 ° C, the malonate adducts 4b and 5a (61:39) were isolated in 6% yield
    • Using 3b in DME, no trapping was observed at room temperature, and at 40 ° C, the malonate adducts 4b and 5a (61:39) were isolated in 6% yield.
  • 21
    • 33846229765 scopus 로고    scopus 로고
    • From 3e, 6b was formed in 53% yield after 14 h
    • From 3e, 6b was formed in 53% yield after 14 h.
  • 22
    • 33846256772 scopus 로고    scopus 로고
    • 2 was inefficient, leading solely to dimerization as determined by GCMS.
    • 2 was inefficient, leading solely to dimerization as determined by GCMS.
  • 23
    • 33846243012 scopus 로고    scopus 로고
    • No dimerization or cyclopropanation took place in the absence of a palladium catalyst. Starting material was quantitatively recovered
    • No dimerization or cyclopropanation took place in the absence of a palladium catalyst. Starting material was quantitatively recovered.
  • 24
    • 33846236042 scopus 로고    scopus 로고
    • No cyclopropanation was observed under Trost's conditions.
    • No cyclopropanation was observed under Trost's conditions.
  • 25
    • 33846190318 scopus 로고    scopus 로고
    • Determined by NOE experiments see the Supporting Information
    • Determined by NOE experiments (see the Supporting Information).
  • 26
    • 33846256337 scopus 로고    scopus 로고
    • Slow addition of the substrate did not improve the yields
    • Slow addition of the substrate did not improve the yields.
  • 27
    • 33646446776 scopus 로고    scopus 로고
    • Recent vinylcyclopropanation methods: (a) Tseng, N.-W.; Mancuso, J.; Lautens, M. J. Am. Chem. Soc. 2006, 128, 5338-5339.
    • Recent vinylcyclopropanation methods: (a) Tseng, N.-W.; Mancuso, J.; Lautens, M. J. Am. Chem. Soc. 2006, 128, 5338-5339.
  • 32
    • 33846262220 scopus 로고    scopus 로고
    • Repeated chromatography was required to separate the starting alkene from the [2+1] cycloadduct, thus limiting the isolated yield of pure product
    • Repeated chromatography was required to separate the starting alkene from the [2+1] cycloadduct, thus limiting the isolated yield of pure product.
  • 33
    • 33746369797 scopus 로고    scopus 로고
    • [l,3]-Ru-carbene shift: (a) Ohe, K.; Fujita, M.; Matsumoto, H.; Tai, Y.; Miki, K. J. Am. Chem. Soc. 2006, 128, 9270-9271.
    • [l,3]-Ru-carbene shift: (a) Ohe, K.; Fujita, M.; Matsumoto, H.; Tai, Y.; Miki, K. J. Am. Chem. Soc. 2006, 128, 9270-9271.
  • 37
    • 33846236588 scopus 로고    scopus 로고
    • All products had >98% deuterium incorporation and were one stereoisomer, except for 3-d-5a, isolated as a 1:1 (E:Z) mixture.
    • All products had >98% deuterium incorporation and were one stereoisomer, except for 3-d-5a, isolated as a 1:1 (E:Z) mixture.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.