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

Tetrahedron Letters

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

  Bricout, Hervé ^a   Carpentier, Jean François ^a   Mortreux, André ^a  

^a Ecole Nationale Superieure de Chimie de Lille   (France)

Author keywords

[No Author keywords available]

Indexed keywords

MALONIC ACID DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; DRUG SYNTHESIS; IN VITRO STUDY; ISOMERISM; METHODOLOGY; REACTION ANALYSIS;

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

References (18)

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2. (b) Heck, R. F. in Palladium Reagents in Organic Synthesis, Academic Press, New York, 1985.
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11. (f) Kobayashi, Y.; Ikeda, E. J. Chem. Soc., Chem. Commun. 1994, 1789-1790.
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14. 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.
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16. 6. Bricout, H.; Carpentier, J.-F.; Mortreux, A. Tetrahedron Letters 1996, 37, 6105-6108.
17. 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.
18. 8. Yamagishi, M.; Shima, T.; Yamagishi, T.; Hida, M. Tetrahedron: Asymmetry 1991, 2, 663-666.