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Volumn 38, Issue 6, 1997, Pages 1053-1056

Further developments in metal-catalysed C-C bond cleavage in allylic dimethyl malonate derivatives

Author keywords

[No Author keywords available]

Indexed keywords

MALONIC ACID DERIVATIVE;

EID: 0031562044     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02510-5     Document Type: Article
Times cited : (29)

References (18)
  • 1
    • 84942767100 scopus 로고
    • Wilkinson, G.; Stone, F. G. A.; Abel, E. W., Pergamon, Oxford, U.K., Ch. 8
    • 1. For leading references, see: (a) Trost, B. M.; Verhoeven, T. R. in Comprehensive Organometallic Chemistry; (Eds.: Wilkinson, G.; Stone, F. G. A.; Abel, E. W.), Pergamon, Oxford, U.K., 1982, Ch. 8, pp 799-938.
    • (1982) Comprehensive Organometallic Chemistry , pp. 799-938
    • Trost, B.M.1    Verhoeven, T.R.2
  • 3
    • 0346602829 scopus 로고
    • (c) Tsuji, J. Tetrahedron 1986, 42, 4361-4401.
    • (1986) Tetrahedron , vol.42 , pp. 4361-4401
    • Tsuji, J.1
  • 14
    • 0011294758 scopus 로고    scopus 로고
    • 2 (36 mg, 0.13 mmol) was added a solution of dppb (112 mg, 0.26 mmol) in DMF (12.5 ml) under nitrogen. After 15 min stirring, dimethyl diallylmalonate (6) (0.69 g, 3.25 mmol), DMM (1.73 g, 13 mmol, 4 eq.) and ethylbenzene (0.21 g, 2 mmol) as an internal standard were added. The solution was stirred at 100 °C and the reaction was monitored by GC analysis of aliquot samples. After 165 h, 7 was isolated from the reaction mixture by chromatography and fully characterised by NMR and MS techniques
    • 2 (36 mg, 0.13 mmol) was added a solution of dppb (112 mg, 0.26 mmol) in DMF (12.5 ml) under nitrogen. After 15 min stirring, dimethyl diallylmalonate (6) (0.69 g, 3.25 mmol), DMM (1.73 g, 13 mmol, 4 eq.) and ethylbenzene (0.21 g, 2 mmol) as an internal standard were added. The solution was stirred at 100 °C and the reaction was monitored by GC analysis of aliquot samples. After 165 h, 7 was isolated from the reaction mixture by chromatography and fully characterised by NMR and MS techniques.
  • 17
    • 0011285869 scopus 로고    scopus 로고
    • Several control experiments (i without metal precursor and dppb, and (ii) without metal precursor but in the presence of dppb showed that no racemization at all occurs without the Ni-or Pd-based catalyst. The use of NaDMM is essential for a reasonable activity
    • 7. Several control experiments ((i) without metal precursor and dppb, and (ii) without metal precursor but in the presence of dppb) showed that no racemization at all occurs without the Ni-or Pd-based catalyst. The use of NaDMM is essential for a reasonable activity.


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