Abstract
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.
Original language | English |
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Pages (from-to) | 682-690 |
Number of pages | 9 |
Journal | Tetrahedron Asymmetry |
Volume | 19 |
Issue number | 6 |
DOIs | |
Publication status | Published - 2008 Apr 3 |
ASJC Scopus subject areas
- Catalysis
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry