Liquid and solid phase syntheses of orthogonally protected α-hydrazinoacid derivatives

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• 作者：Bouillon ; Isabelle ; Brosse ; Nicolas ; Vanderesse ; Ré ; gis ; Jamart-Gré ; goire ; Brigitte
• 关键词：Solid phase organic synthesis ; α ; -Hydrazinoacid ; Mitsunobu reaction ; Protecting group
• 刊名：Tetrahedron Letters
• 出版年：2004
• 出版时间：April 26, 2004
• 年：2004
• 卷：45
• 期：18
• 页码：3569-3572
• 全文大小：253 K

文摘

The first solid phase synthesis of chiral α-hydrazinoacids has been developed. This synthesis was achieved by the preparation of solid supported-N-alkyloxycarbonyl-aminophthalimides used as acidic partners in the Mitsunobu protocol involving α-hydroxyesters. Two different final trans-protection steps of the phthaloyl group, developed first in liquid phase, result in efficient releases of orthogonally bis-protected or fully tris-protected hydrazine derivatives. A comparison between liquid and solid phase syntheses is outlined: even if the overall yields are sometimes rather higher by the liquid phase synthesis, the on-resin protocol is much more rapid and convenient than the liquid protocol.