96240-08-3Relevant articles and documents
A New Route to Cyclic Amines by Anionic Cyclization
Coldham, Iain,Hufton, Richard
, p. 2157 - 2160 (1995)
Transmetallation of an aminomethylstannane gives rise to an aminomethyllithium which undergoes an anionic cyclization onto an unactivated alkene.The resulting organolithium reincorporates trimethyltin to give the product cyclic amine.The cyclization can b
A hydrogen borrowing annulation strategy for the stereocontrolled synthesis of saturated aza-heterocycles
Armstrong, Roly J.,Chamberlain, Anna E. R.,Donohoe, Timothy J.,Paterson, Kieran J.,Twin, Heather C.
supporting information, p. 3563 - 3566 (2020/04/03)
An iridium catalyzed method for the synthesis of saturated aza-heterocycles from amines and diols is reported. A wide range of substituted heterocycles can be obtained using this approach including products bearing substituents at the C2, C3 and C4 positions. Employing water as the solvent, enantiopure diols could undergo annulation with minimal racemization, enabling the synthesis of valuable enantioenriched C3 and C4-substituted saturated aza-heterocycles.
Synthesis of 3-alkylpyrrolidines by anionic cyclization
Coldham, Iain,Hufton, Richard
, p. 12541 - 12552 (2007/10/03)
α-Aminocarbanions, generated by transmetallation of aminomethylstannaes, cyclize onto an unactivated alkene to give 3-alkylpyrrolidines. The intermediate organolithium either reincorporates trimethyltin or, from the tributylstannanes, can be trapped with a variety of electrophiles. From the trimethylstannane, the cyclization can be promoted catalytically using 0.2 equivalents of methyllithium. The trimethyltin group in the product can be cleaved using ceric ammonium nitrate. Trapping the 3-lithiomethylpyrrolidine with ethylchloroformate, followed by hydrolysis provides a four step synthesis of the GABA uptake inhibitor 3-pyrrolidineacetic acid.
