263407-98-3Relevant academic research and scientific papers
The partial reduction of heterocycles: An alternative to the birch reduction
Donohoe, Timothy J.,Harji, Rakesh R.,Cousins, Rick P. C.
, p. 1331 - 1334 (2000)
The partial reduction of a series of heterocycles in THF is described. By adding amine 3 as a proton source and naphthalene as an electron carrier, we were able to produce reductively alkylated pyrrolines and dihydrofurans in moderate to good yields. This reaction does not require liquid ammonia as a solvent, which may have interesting ramifications for large-scale synthesis. Moreover, we were also able to quench the reduction reactions with an acid chloride so performing a reductive acylation reaction. (C) 2000 Elsevier Science Ltd.
Diastereoselective reductive aldol reactions of Boc-protected electron deficient pyrroles
Donohoe, Timothy J.,House, David
, p. 1095 - 1098 (2003)
An anti-selective reductive aldol reaction of a Boc-protected, 2-substituted pyrrole is reported. Reduction with LiDBB generates an exocyclic lithium enolate, but optimal stereoselectivity is obtained by transmetallation to magnesium with MgBr2·OEt2. The corresponding syn-aldols can easily be obtained (protected as carbamates) by subsequent inversion.
Reductive aldol reactions on aromatic heterocycles
Donohoe, Timothy J.,Ace, Karl W.,Guyo, Paul M.,Helliwell, Madeleine,McKenna, Jeffrey
, p. 989 - 993 (2000)
The Birch reduction of both pyrroles and furans can be quenched with an aldehyde electrophile, thus constituting a reductive aldol reaction. Although the reaction was not stereoselective, the pyrrolines derived from reduction of pyrroles could be oxidised and then reduced with NaBH4 to provide syn- aldol adducts with high levels of stereoselectivity. The relative stereochemistry of two adducts was proven by X-ray crystallography. (C) 2000 Elsevier Science Ltd.
