Selective O-Allylation of Amidoalcohols on Solid Support

Synlett

Volumn 1996, Issue 4, 1996, Pages 389-391

  Motorina, Irina A ^a   Parly, Florence ^a   Grierson, David S ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002582896     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5416     Document Type: Article

References (29)

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2. For reviews on the subject see: (a) McKillop, A.; Young, D.W. Synthesis , 1979, 401, 481; (b) Solid Supports and Catalysts in Organic Synthesis, Smith, K. Ed. Ellis Horwood, 1992; (c) Posner, G.H. Angew. Chem. Int. Ed. Engl., 1978, 17, 487.
3. For reviews on the subject see: (a) McKillop, A.; Young, D.W. Synthesis , 1979, 401, 481; (b) Solid Supports and Catalysts in Organic Synthesis, Smith, K. Ed. Ellis Horwood, 1992; (c) Posner, G.H. Angew. Chem. Int. Ed. Engl., 1978, 17, 487.
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17. Alumina (Merck, art. 1097) was dried by heating for 2-3 days at 170°C in an oven or during 4 h at 200°C in vacuo . In both instances the adsorbent was brought to room temperature under vacuum.
18. 2, acetone and methanol. The combined washings were concentrated, and the crude product was flash column chromatographed on silica gel.
19. 3 ([M+H]): m/z 232.0974; found: 232.0961.
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23. Formation of 5 through allylic oxidation of 2a seems to be unlikely as accumulation of the O-acryloyl product was not observed for other substrates (3a-c), even after 1-2 weeks in contact with alumina. In another experiment, allylation of 2-acetamidobenzyl alcohol leads to a mixture of the corresponding O-allyl ether and the product of acyl migration - 2-(N,N-diallylamino)benzyl acetate.
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29. 10