214752-01-9Relevant articles and documents
Asymmetric Strecker reaction of N-benzhydrylimines utilising new tropos biphenyldiol-based ligands
Wuennemann, Stefan,Froehlich, Roland,Hoppe, Dieter
, p. 684 - 692 (2008/09/17)
The synthesis of a library of N-arenesulfonyl-1,3-oxazolidinyl-substituted biphenyldiols is presented. A set of two central intermediates together with easily accessible N-arenesulfonylamino alcohols furnish a broad variety of 1,3-oxazolidines. These are applied as chiral tropos ligands in a titanium-mediated Strecker-type reaction of N-benzhydrylimines. A correlation between the ee values in the product and the diastereomeric ratio concerning the chiral axis of the ligand is made. Those substituents in the ligand which proved to lead to a higher preference for one diastereomeric conformer of the chiral axis in related compounds now provide the most selective ligands. Two privileged ligands are identified that afford superior results in 8 of 13 screenings. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Reactions of n-arylsulfonyl-2,3-cis- and n-arylsulfonyl-2,3-frans-3-alkyl-2-vinylaziridines with organocopper reagents: importance of 2,3-cis-stereochemistry in controlling regio- and stereoselectivity
Toda, Ayako,Aoyama, Hiroshi,Mimura, Norio,Ohno, Hiroaki,Fujii, Nobutaka,Ibuka, Toshiro
, p. 7053 - 7061 (2007/10/03)
Although reactions of 2,3-trans-N-arylsulfonyl-3-alkyl-2-alkenylaziridines with organocopper reagents give a mixture of two or three products, the corresponding 2,3-cis-isomers provide a highly efficient route to synthetically important nonracemic CE)-allylamines. It is also found that the reaction proceeds via the well-known anti-SN2′ pathway.