88381-96-8Relevant academic research and scientific papers
Stereoselective synthesis of pyrrolidines and pyrrolizidines by intramolecular carbolithiation
Coldham,Hufton,Price,Rathmell,Snowden,Vennall
, p. 1523 - 1531 (2007/10/03)
Methods for the preparation of substituted homoallylic amines and their conversion to pyrrolidines or pyrrolizidines are described. N-Alkylation of a variety of homoallylic secondary amines with (tributylstannyl)methyl methanesulfonate and subsequent tinlithium exchange, generates organolithium species that undergo intramolecular carbolithiation (anionic cyclization). High stereoselectivities in the cyclization, particularly for the formation of 2,4-disubstituted pyrrolidines, are obtained.
Indium mediated Barbier-type allylation of aldimines in alcoholic solvents
Vilaivan, Tirayut,Winotapan, Chutima,Shinada, Tetsuro,Ohfune, Yasufumi
, p. 9073 - 9076 (2007/10/03)
Barbier-type allylation of unactivated aldimines with allyl bromides in the presence of indium powder took place rapidly in alcoholic solvents to give homoallylic amines in fair to good yields.
Stereoselective anionic cyclizations to pyrroldines
Coldham, Iain,Hufton, Richard,Rathmell, Richard E.
, p. 7617 - 7620 (2007/10/03)
Cyclization of α-amino-organolithiums onto unactivated alkenes results in the formation of 2,4-disubstituted pyrrolidines with high selectivities in favour of the cis isomers. The use of the α-methylbenzyl chiral auxiliary on the nitrogen atom gives rise
Synthesis of azetidines by electrophilic selenium-induced cyclization of homoallylic benzylamines
Berthe, Benedicte,Outurquin, Francis,Paulmierz.ast, Claude
, p. 1393 - 1396 (2007/10/03)
Homoallyl benzylamines prepared by allylation of the corresponding N-benzylimines, have been subjected to a selenium-induced cyclization under various conditions. At room temperature. the 4-exo and the 5-endo modes are competitive. In acetonitrile, the azetidine has been isolated as the major cyclization product, especially for homoallylamines derived from ketimines. With an excess or selenium reagent, 3-halopyrrolidines have been obtained.
Addition of Allylboronates to Schiff Bases and to Oximes
Hoffmann, Reinhard W.,Eichler, Guenter,Endesfelder, Andreas
, p. 2000 - 2007 (2007/10/02)
Clean addition of allylboronates of Type 3 to Schiff bases 2 leads to the secondary homoallylamines 4.Analogous addition to the oximes 9 results in the formation of the hydroxylamines 13.The latter allow the generation of the primary homoallylamines 14.
