- One-Pot Reductive Allylation of Amides by Using a Combination of Titanium Hydride and an Allylzinc Reagent: Application to a Total Synthesis of (-)-Castoramine
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A one-pot direct reductive allylation protocol has been developed for the synthesis of secondary amines by using titanium hydride and an allylzinc reagent. This protocol is applicable to a broad range of substrates, including acyclic amides, benzamides, α,β-unsaturated amides, and lactams. The stereochemical outcome obtained from the reaction with crotylzinc reagent suggested that the allylation reaction proceeds through a six-membered cyclic transition state. A total synthesis of (-)-castoramine was accomplished by following this protocol for the highly stereoselective construction of contiguous stereocenters.
- Itabashi, Suguru,Shimomura, Masashi,Sato, Manabu,Azuma, Hiroki,Okano, Kentaro,Sakata, Juri,Tokuyama, Hidetoshi
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supporting information
p. 1786 - 1790
(2018/07/03)
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- SYNTHESIS OF ALIPHATIC AMINES RELATED TO MONODANSYLCADAVERINE VIA THE OXIDATIVE REARRANGEMENT OF ALIPHATIC AMIDES WITH PHENYL IODOSYL BIS(TRIFLUOROACETATE)
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A series of aliphatic primary amides have been oxidatively rearranged to primary amines with phenyl iodosyl(trifluoroacetate).Sulfonamide groups on the substrates have not been affected.
- Pavlidis, V. H.,Chan, E. D.,Pennington, L.,McParland, M.,Whitehead, M.
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p. 1615 - 1624
(2007/10/02)
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- Synthesis of Macrotricyclic Amines
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The synthesis of the macrotricyclic amines 14a and b with a tetrahedron skeleton is achieved by three successive cyclisations using high dilution conditions (overall yields 5.6 and 2.5percent, resp.).
- Schmidtchen, Franz P.
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p. 864 - 874
(2007/10/02)
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