1023743-82-9Relevant academic research and scientific papers
Amines bearing tertiary substituents by tandem enantioselective carbolithiation-rearrangement of vinylureas
Tait, Michael,Donnard, Morgan,Minassi, Alberto,Lefranc, Julien,Bechi, Beatrice,Carbone, Giorgio,O'Brien, Peter,Clayden, Jonathan
supporting information, p. 34 - 37 (2013/03/28)
In the presence of (-)-sparteine or a (+)-sparteine surrogate, organolithiums add to N-alkenyl-N'-arylureas to give benzylic organolithiums in an enantioselective manner. Under the influence of DMPU, these organolithiums undergo rearrangement with migrati
Rhodium-catalyzed asymmetric arylation of N -(tert -butanesulfinyl)imines with sodium tetraarylborates
Reddy, Leleti Rajender,Gupta, Aditya P.,Villhauer, Eric,Liu, Yugang
experimental part, p. 1095 - 1100 (2012/03/12)
A diastereoselective rhodium-catalyzed arylation of N-(tert-butanesulfinyl) imines with sodium tetraarylborates is described. This method is general for constructing various chiral α-branched amines and 2-substituted pyrrolidines with high diastereoselectivity. A practical asymmetric approach to access chiral amines has been developed involving the use of air-stable Rh catalysts and reagents and in the absence of an external ligand.
An improved procedure for the diastereoselective addition of triorganozincates to N-(tert-butanesulfinyl)imines: use of catalytic dialkylzinc
Almansa, Raquel,Guijarro, David,Yus, Miguel
supporting information; scheme or table, p. 3198 - 3201 (2009/08/17)
The addition of triorganozincates to (R)-N-(tert-butanesulfinyl)benzaldimine has been performed with very good results by using a catalytic amount of Me2Zn (0.15 equiv) to generate the organozincate. Yields and/or diastereoselectivities of the
Synthesis of highly enantiomerically enriched amines by the diastereoselective addition of triorganozincates to N-(tert-butanesulfinyl)imines
Almansa, Raquel,Guijarro, David,Yus, Miguel
experimental part, p. 2484 - 2491 (2009/04/11)
The reaction of triorganozincates with (R)-N-(tert-butanesulfinyl) imines gives the expected α-branched sulfinamides in good to excellent yields with diastereomeric ratios of up to 98:2. The N-sulfinyl group of the products can be easily removed by acidic treatment, affording the corresponding chiral primary amines in enantiomeric excesses of up to 96%. The reactivity and the selectivity shown by the triorganozincates are different from the ones observed with the corresponding Grignard reagents, which allows, in several cases, the preparation of both enantiomers of an amine from the same imine substrate. When mixed triorganozincates are used, one can take advantage of the slow transfer rate of the methyl group to use it as a non-transferable one. Both aromatic and aliphatic aldimines, as well as activated ketimines, are good substrates for these addition reactions.
