| Synthesis of Chiral 2,5—Bis（oxazolinyl） thiophenes and Their Application as Chiral Shift Reagents for 1,1′—Bi—2—naphthol |
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| 引用本文： | GAO，Ming－Zhang WANG，Bo 等.Synthesis of Chiral 2,5—Bis（oxazolinyl） thiophenes and Their Application as Chiral Shift Reagents for 1,1′—Bi—2—naphthol[J].中国化学,2002,20(1):85-89. |
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| 作者姓名： | GAO，Ming－Zhang WANG，Bo |
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| 作者单位： | DepartmentofChemistry，ZhongshanUniversity,Guangzhou,Guangdong510275,China |
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| 基金项目： | theNationalNaturalScienceFoundationofChina (No.2 9770 5 7)andGuangdongNaturalScienceFoundation |
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| 摘 要： | A series of C2-symmetrical chiral 2,5-bis (4′-alkyloxazolin-2-yl) thiophenes (thiobox) have been synthesized from thiophene-2,5-dicarboxylic acid by sequential amidation with a chiral ethanolamine,conversion of hydroxyl to chloro group, and base-promoted oxazoline ring formation.As demonstrated by (-)-2,5-bis4′-(S)-isopropyloxazolin-2′-yl] thiophene,these thiobox systems exhibited remarkable chirality recognition of 1,1′-bi-2-naphthol giving rise to pronounced shifts in the ^1H NMR signals of the latter axial chiral compound at the positions of C-3,C-4,C-5,and C-8.
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| 关 键 词： | 合成 手性化合物 手性2，5－二唑啉基噻吩 手性位移试剂 1，1′－二－2－萘酚 |
Synthesis of Chiral 2,5‐Bis(oxazolinyl)thiophenes and Their Application as Chiral Shift Reagents for 1,1′‐Bi‐2‐naphthol |
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| GAO,Ming-Zhang WANG,Bo LIU,Han-Biao XU,Zun-Le.Synthesis of Chiral 2,5‐Bis(oxazolinyl)thiophenes and Their Application as Chiral Shift Reagents for 1,1′‐Bi‐2‐naphthol[J].Chinese Journal of Chemistry,2002,20(1):85-89. |
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| Authors: | GAO Ming-Zhang WANG Bo LIU Han-Biao XU Zun-Le |
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| Institution: | GAO,Ming-Zhang WANG,Bo LIU,Han-Biao XU,Zun-LeDepartment of Chemistry,Zhongshan University,Guangzhou,Guangdong 510275,China |
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| Abstract: | A series of C2‐symmetrical chiral 2,5‐bis(4′‐alkyloxazolin‐2‐yl) thiophenes (thiobox) have been synthesized from thiophene‐2, 5‐dicarboxylic acid by sequential amidation with a chiral ethanolamine, conversion of hydroxyl to chloro group, and base‐promoted oxazoline ring formation. As demonstrated by ( ‐ )‐2, 5‐Ws4′‐( S)‐isopropyloxazolin‐2′‐yl] thiophene, these thiobox systems exhibited remarkable chirality recognition of 1, 1′‐bi‐2‐naphthol giving rise to pronounced shifts in the lH NMR signals of the latter axial chiral compound at the positions of C‐3, C‐4, C‐5, and C‐8. |
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| Keywords: | C 2-symmetry 2 5-bis(oxazolinyl)thiophene chiral shift reagent |
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