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: 4-三月-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
顯示於類別:期刊論文


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