Practical one-pot and large-scale synthesis of N-(tert-butyloxycarbonyl)-3- pyrroline
N-(tert-Butyloxycarbonyl)-3-pyrroline was prepared with high purity in large scale starting from cis-1,4-dichloro-2-butene via delepine reaction and subsequent cyclization in the presence of potassium carbonate followed by N-Boc protection in methanol.Judicious selection of base and solvent led to the use of a single solvent, i.e., methanol, for cyclization as well as for N-Boc protection to render the one-pot process from compound 2 more practical and greener than the stepwise version.
Heterocyclic lithium amides as chiral ligands for an enantioselective hydroxyalkylation with n-BuLi
(Chemical Equation Presented) Chiral heterocyclic structures based on 3-aminopyrrolidines (3APs), 3-aminotetrahydrothiophens (3ATTs), and 3-aminotetrahydrofurans (3ATFs) have been synthesized. The corresponding lithium amides have been evaluated as chiral ligands in the condensation of n-BuLi on o-tolualdehyde. The returned levels of induction were in the 46-80% ee range. The cheap and easily prepared 3ATFLi's turned out to be also the best ligands, giving access to the expected R or S alcohols in a same 80% level of induction at -78°C in THF. In all cases, the sense of induction depends on the absolute configuration of C8 on the 3-amino appendage. A general concept is proposed to rationalize the process of induction in the presence of organolithium species.
Duguet, Nicolas,Petit, Sylvain M.,Marchand, Philippe,Harrison-Marchand, Anne,Maddaluno, Jacques
p. 5397 - 5409
(2008/12/21)
3-pyrroline: [1H-pyrrole, 2,5-dihydro-]
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Meyers, Albert I.,Warmus, Joseph S.,Dilley, Garrett J.,Gillman, Kevin W.,Hart, David J.
p. 246 - 246
(2017/09/15)
A Modified Procedure for the Preparation of 2,5-Dihydropyrrole (3-Pyrroline)
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Warmus, Joseph S.,Dilley, Garrett J.,Meyers, A. I.
p. 270 - 271
(2007/10/02)
A Convenient Route to 3-Pyrroline Utilizing the Delepine Reaction
3-Pyrroline(2,5-dihydro-1H-pyrrole) has been prepared from (Z)-1,4-dichloro-2-butene (1) in three steps in an overall yield of 74percent.
Brandaenge, Svante,Rodriguez, Benito
p. 347 - 348
(2007/10/02)
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