Totally Selective Reaction of CO2 with Enantiopure Amino Epoxides under Mild Reaction Conditions. Synthesis and Synthetic Applications of Enantiopure (4R,1'S)- or (4S,1

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• 作者：José ; M. Concelló ; n ; Virginia del Solar ; Santiago Garc&iacute ; a-Granda ; M. Rosario D&iacute ; az
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：September 28, 2007
• 年：2007
• 卷：72
• 期：20
• 页码：7567 - 7573
• 全文大小：115K
• 年卷期：v.72,no.20(September 28, 2007)
• ISSN：1520-6904

文摘

D=jo070829xn00001>The reaction of chiral (2R,1'S)- or (2S,1'S)-2-(1-aminoalkyl)epoxides 1 or 2 with CO₂, generated fromacidic treatment of an aqueous solution of NaHCO₃ at room temperature, efficiently afforded enantiopurecyclic carbonates 3 or 4, respectively, with total selectivity. Compounds 3 and 4 were readily transformedinto the corresponding diols 7 and 8 by reaction with LiAlH₄ or by basic hydrolysis. When compounds3 or 4 were allowed to react with methyllithium at -78 C, O¹-acetylalkane-1,2-diols 9 and 10 wereobtained with total or high selectivity.