760197-72-6Relevant articles and documents
On the scope of diastereoselective aziridination of various chiral auxiliaries derived N- and O-enones with N-aminophthalimide in the presence of lead tetraacetate
Duan, Pei-Wen,Chiu, Ching-Chen,Lee, Wei-Der,Pan, Li Shiue,Venkatesham, Uppala,Tzeng, Zheng-Hao,Chen, Kwunmin
, p. 682 - 690 (2008/09/20)
The treatment of a range of N- and O-enones derived from various camphor-based chiral auxiliaries A-D with N-aminophthalimide in the presence of lead tetraacetate is described. In general, N-phthalimidoaziridines were obtained with high diastereoselectivities (up to 98% de) and chemical yields (up to 95%) when 10,10-diphenyl-2,10-camphanediol A derived O-enones with a range of substituents were used under the same reaction conditions. Excellent stereoselectivity was obtained when the N-tosyl camphorpyrazolidinone E derived acrylate was used. The absolute configuration of the new stereogenic center(s) of the major diastereomer was established by X-ray crystallographic analysis. Chiral auxiliary cleavage was achieved under mild reaction conditions. A model to explain the stereochemical induction is also proposed.