Alkylation of ketone and ester lithium enolates with nitroethylene

Tetrahedron Letters

Volumn 40, Issue 24, 1999, Pages 4485-4488

  Flintoft, Rebecca J ^a   Buzby, Jennifer C ^a   Tucker, John A ^a,b  

^a Medicinal Chemistry Research   (United States)

^b ELAN PHARMACEUTICALS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER DERIVATIVE; KETONE DERIVATIVE; LITHIUM DERIVATIVE;

ALKYLATION; ARTICLE; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 0033546093     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00814-X     Document Type: Article

References (24)

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20. 21. For the alkylation of enamines with nitroethylene, see Kuehne, M. E.; Foley, L. J. Org. Chem. 1965, 30, 4280-4284.
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22. 23. When the reaction described in entry 2 of Table 2 was performed using the lithium salt of 2,2,6,6-tetramethylpiperidine as base, only traces of the desired conjugate addition product were obtained.
23. 24. Nitroethylene was prepared according to Buckley, G. D.; Scaife, C. W. J. Chem. Soc. 1947, 1471. Best results were obtained when nitroethylene was distilled from the nitroethanol/phthalic anhydride mixture over a period of about 45 minutes. The crude nitroethylene was redistilled at 45 °C/80 torr. Older bottles of nitroethanol which had turned dark gave a product which could not readily be purified. Nitroethylene appears to be stable for several months when stored in the dark at -15 °C. The bottle should be returned to the freezer promptly after transfer of the required amount.
24. 25. In the reaction described by entry 10 of Table 2, addition of a 25 °C solution of nitroethylene gave results similar to those obtained with a -78 °C solution of nitroethylene.