基于苹果酰亚胺的不对称合成方法学研究进展 |
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引用本文: | 黄培强.基于苹果酰亚胺的不对称合成方法学研究进展[J].有机化学,2001,21(11):1065-1073. |
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作者姓名: | 黄培强 |
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作者单位: | 厦门大学化学系, |
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基金项目: | 国家杰出青年科学基金(№.29625204)和国家自然科学基金(Nos.29100007,29572065,29832020,20072031)资助项目. |
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摘 要: | 综述了以苹果酰亚胺为手性吡咯烷(酮)合成子等效体的合成方法学研究进展。通过新建立的高度区域和立体选择性的灵活多用的不对称还原烷基化方法,可方便地合成反式-5-烷基-4-羟基-2-吡咯烷酮,进而转化为反式-2-烷基-3-羟基(胺基)吡咯烷和反侧-Υ-烷基-Υ-氨基-β-羟基酸。由此打开了通向依莫必利,茴香霉素,pyrrolamA,hapalosin的Υ-氨基酸片断和statine类似物(3S,4R)-ACHPA活化形式的多用途合成路线。
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关 键 词: | 酰亚胺 烷基化 吡咯烷P 吡咯烷酮P 苹果酸P 不对称反应 |
修稿时间: | 2001年7月19日 |
Progress in the asymmetric synthetic methodology based on malimides |
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Institution: | Xiamen Univ, Dept Chem.Xiamen(361005) |
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Abstract: | Progress in the asymmetric synthetic methodology based on the use of malimides as synthetic equivalents to substituted 2-pyrrolidinones is summarized. The versatile, regio- and diastereo-selective reductive alkylation method developed in these laboratories allows the easy access to trans-5-alkyl-4-benzyloxy-2-pyrrolidinones, which could be further transformed into trans-2-alkyl-3-hydroxypyrroliines or anti-Υ -alkyl-Υ-amino-β-hydroxy acids. The studies along this array thus open an avenue to the asymmetric synthesis of nemonapride, anisomycin, pyrrolam A, the Υ-amino-β-hydroxy acid residue of hapalosin as well as an activated form of (3S, 4R)-ACHPA, a statine analogue. |
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Keywords: | IMIDE ALKYLATION PYRROLIDINE P PYRROLIDONE P MALIC ACID P |
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