摘要
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.
原文 | 英語 |
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頁(從 - 到) | 682-690 |
頁數 | 9 |
期刊 | Tetrahedron Asymmetry |
卷 | 19 |
發行號 | 6 |
DOIs | |
出版狀態 | 已發佈 - 2008 4月 3 |
ASJC Scopus subject areas
- 催化
- 物理與理論化學
- 有機化學
- 無機化學
指紋
深入研究「On the scope of diastereoselective aziridination of various chiral auxiliaries derived N- and O-enones with N-aminophthalimide in the presence of lead tetraacetate」主題。共同形成了獨特的指紋。資料集
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CCDC 655364: Experimental Crystal Structure Determination
Duan, P. (Creator), Chiu, C. (Creator), Lee, W. (Creator), Pan, L. S. (Creator), Venkatesham, U. (Creator), Tzeng, Z. (Creator) & Chen, K. (Creator), Unknown Publisher, 2008
DOI: 10.5517/ccpzysc, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccpzysc&sid=DataCite
資料集: Dataset
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CCDC 655363: Experimental Crystal Structure Determination
Duan, P. (Creator), Chiu, C. (Creator), Lee, W. (Creator), Pan, L. S. (Creator), Venkatesham, U. (Creator), Tzeng, Z. (Creator) & Chen, K. (Creator), Unknown Publisher, 2008
DOI: 10.5517/ccpzyrb, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccpzyrb&sid=DataCite
資料集: Dataset
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CCDC 655362: Experimental Crystal Structure Determination
Duan, P. (Creator), Chiu, C. (Creator), Lee, W. (Creator), Pan, L. S. (Creator), Venkatesham, U. (Creator), Tzeng, Z. (Creator) & Chen, K. (Creator), Unknown Publisher, 2008
DOI: 10.5517/ccpzyq9, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccpzyq9&sid=DataCite
資料集: Dataset