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 |
|---|---|
| Pages (from-to) | 682-690 |
| Number of pages | 9 |
| Journal | Tetrahedron Asymmetry |
| Volume | 19 |
| Issue number | 6 |
| DOIs | |
| Publication status | Published - 2008 Apr 3 |
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ASJC Scopus subject areas
- Catalysis
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry
Cite this
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.
In: Tetrahedron Asymmetry, Vol. 19, No. 6, 03.04.2008, p. 682-690.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - On the scope of diastereoselective aziridination of various chiral auxiliaries derived N- and O-enones with N-aminophthalimide in the presence of lead tetraacetate
AU - Duan, Pei Wen
AU - Chiu, Ching Chen
AU - Lee, Wei Der
AU - Pan, Li Shiue
AU - Venkatesham, Uppala
AU - Tzeng, Zheng Hao
AU - Chen, Kwunmin
PY - 2008/4/3
Y1 - 2008/4/3
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=41449084757&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=41449084757&partnerID=8YFLogxK
U2 - 10.1016/j.tetasy.2008.02.028
DO - 10.1016/j.tetasy.2008.02.028
M3 - Article
AN - SCOPUS:41449084757
VL - 19
SP - 682
EP - 690
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
SN - 0957-4166
IS - 6
ER -