Syntheses of Chiral 尾- and 纬-Amino Ethers, Morpholines, and Their Homologues via Nucleophilic Ring-Opening of Chiral Activated Aziridines and Azetidines

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• 作者：Manas K. Ghorai ; Dipti Shukla ; Aditya Bhattacharyya
• 刊名：The Journal of Organic Chemistry
• 出版年：2012
• 出版时间：April 20, 2012
• 年：2012
• 卷：77
• 期：8
• 页码：3740-3753
• 全文大小：570K
• 年卷期：v.77,no.8(April 20, 2012)
• ISSN：1520-6904

文摘

Lewis acid catalyzed quaternary ammonium salt mediated highly regioselective ring-opening of chiral activated aziridines and azetidines with alcohols to nonracemic 尾- and 纬-amino ethers has been developed. The reaction mainly proceeds via an S_N2 pathway, and the partial racemization of the starting substrate was effectively controlled by using quaternary ammonium salts. 尾- and 纬-amino ethers are obtained with high enantio- and diastereospecificity (ee up to >99%, de up to 99%). The methodology was further extended to synthesize morpholines and their homologues with high enantiospecificity (ee up to 90%) when halo alcohols were employed as the nucleophiles.