- P(RNCH2CH2)3N: Efficient 1,4-addition catalysts
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The 1,4-addition of primary alcohols, higher nitroalkanes, and a Schiff's base of an α-amino ester to α,β-unsaturated substrates produces the corresponding products in moderate to excellent yields when carried out at -63 to 70°C in the presence of catalytic amounts of the nonionic strong bases P(RNCH2CH2)3N (R = Me, i-Pr, i-Bu) in isobutyronitrile. Diastereoselectivity for the anti form of the product is high in the case of the Schiff's base in the absence of lithium ion. These catalysts are easily removed from the product by either column filtration through silica gel or via aqueous workup.
- Kisanga, Philip B.,Ilankumaran, Palanichamy,Fetterly, Brandon M.,Verkade, John G.
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p. 3555 - 3560
(2007/10/03)
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- SYNTHESIS AND REACTIONS OF 1-AZASPIROCYCLES: 1-AZASPIRODECANE AND 1-AZASPIRONONANE RING SYSTEMS.
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Nitrocyclohexane reacted with methyl acrylate in the presence of Triton-B to yield nitro-ester (4) which cyclised to spirolactam (5) on treatment with zinc in ethanolic hydrochloric acid.Lactam (5) was reduced to pyrrolidine (7) by lithium aluminium hydri
- Bryce, Martin R.,Gardiner, John M.,Horton, Paul J.,Smith, Susan A.
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p. 116 - 124
(2007/10/02)
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