Synthesis of Heterocyclic Cage Compounds and Their Facial Stereoselective Reactions

博士 === 國立交通大學 === 應用化學系 === 89 === Treatment of the compound 6 with electrophilic reagents give the syn addition > anti addition for -facial stereoselecivity. Treatment of the compound 7 with nucleophilic reagents give the syn addition > anti addition for -facial stereoselectivity....

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Bibliographic Details
Main Authors: Hui-Chang Lin, 林煇章
Other Authors: Hsien-Jen Wu
Format: Others
Language:zh-TW
Published: 2001
Online Access:http://ndltd.ncl.edu.tw/handle/22352189963383434961
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Summary:博士 === 國立交通大學 === 應用化學系 === 89 === Treatment of the compound 6 with electrophilic reagents give the syn addition > anti addition for -facial stereoselecivity. Treatment of the compound 7 with nucleophilic reagents give the syn addition > anti addition for -facial stereoselectivity. Compound 26 via Diels-Alder reaction, 1,3-dipolar cycloaddition and electrophilic addition and syn addition products haven’t been detected for their -facial stereoselectivity. Treatment of the compound 73 and 80 with nucleophilic reagents only give the anti addition products for -facial stereoselectivity. Treatment of the compound 91 with electrophilic reagents give the anti addition : syn addition = 82 : 18 for -facial stereoselecivity. Treatment of the compound 96 with nucleophilic reagents give the anti addition : syn addition = 1 : 1 for -facial stereoselecivity. The synthesis of noval carbonyl oxa-cage compound 104 has been accomplished and then reaction of the oxa-cage compound 104 with nucleophilic reagents in dry THF only gave the anti addition compounds for -facial stereoselecivity. Reaction of the thia-cage compounds 106, 107, 108 and 109 with oxidant only gave the anti addition compounds for -facial stereoselecivity. We study the Diels-Alder reaction of pyranes and cyclopentadiene at room temperature. We have found that the substitution can influence the results of Diels-Alder reaction. The synthesis of noval tri-oxa and tetra-oxa cage compounds has been accomplished by iodocyclization and ozonolysis reactions for Diels-Alder products. Treatment of the monothia-, dithia-, and trithia-cage compounds with excess MeSO3H in dichloromethane at 25 ℃ for 10’ regioselectively gave the noval hydride rearrangement products.