標題: | Synthesis of new acetal aza-cage compounds via ozonolysis of bis-endo-diol- and diacylnorbornene derivatives |
作者: | Wu, Chung-Yi Lin, Hui-Chang Wu, Hsien-Jen 應用化學系 Department of Applied Chemistry |
關鍵字: | Aza-cage;Chiral;Ozonolysis;Imine;X-ray |
公開日期: | 4-Mar-2012 |
摘要: | We synthesized acetal aza-cage compounds directly via ozonolysis of 2,3-bis-endo-diol- and diacylnorbornenes in dichloromethane at -78 degrees C. Ozonolysis of the diols followed by addition of amines gave the aza-cage compounds in high yields. The reaction mechanism for the formation of this type of aza-cage compounds is proposed to proceed via the hydroperoxide intermediate. Ozonolysis of the diacetyl norbornene followed by addition of (1) primary amines gave monoaza-cages and diaza-cage, (2) tert-butylamine gave hydroxyl lactone and diaza-cages, and (3) amino acid ester gave optically active aza-cages, in which one compound was converted into chiral aminoalcohol and structure of another was proven by X-ray analysis. A mechanism via the final ozonide and the imine intermediates is proposed for the formation of this type of aza-cages. (C) 2012 Elsevier Ltd. All rights reserved. |
URI: | http://dx.doi.org/10.1016/j.tet.2012.01.055 http://hdl.handle.net/11536/15558 |
ISSN: | 0040-4020 |
DOI: | 10.1016/j.tet.2012.01.055 |
期刊: | TETRAHEDRON |
Volume: | 68 |
Issue: | 9 |
起始頁: | 2100 |
結束頁: | 2106 |
Appears in Collections: | Articles |
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