Completely Stereocontrolled Aldol Reaction of Chiral 尾-Amino Acids

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• 作者：Martin Gazvoda ; Kathrin H枚ferl-Prantz ; Roland Barth ; Wolfgang Felzmann ; Andrej Pevec ; Janez Ko拧mrlj
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：February 6, 2015
• 年：2015
• 卷：17
• 期：3
• 页码：512-515
• 全文大小：345K
• ISSN：1523-7052

文摘

A general protocol to independently access stereoisomerically pure 尾鈥?hydroxy-尾-amino acid derivatives that is based on dibutylboron triflate-mediated aldol reaction of suitably protected 尾-amino acids bearing chiral oxazolidinone auxiliary is reported. The method smoothly afforded syn-aldol (伪,尾鈥?syn) products in pure form and excellent isolated yield. Both 伪,尾-syn and 伪,尾-anti isomers are readily accessible solely through the choice of the oxazolidinone chirality. This method allows for the preparation of stereoisomeric 尾鈥?hydroxy-尾-amino acid derivatives that were previously unreported.