Chemoselective Functionalization of 3,3′-Substituted BINOL Derivatives

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• 作者：Carmine Coluccini ; Antonio Castelluccio ; Dario Pasini
• 刊名：Journal of Organic Chemistry
• 出版年：2008
• 出版时间：June 6, 2008
• 年：2008
• 卷：73
• 期：11
• 页码：4237 - 4240
• 全文大小：266K
• 年卷期：v.73,no.11(June 6, 2008)
• ISSN：1520-6904

文摘

An efficient chemoselective differentiation of vicinal phenolic and benzylic alcohols on optically active binaphthyl skeletons has been achieved via TBS protection of the less sterically hindered, external 3,3′ benzylic positions. Further manipulation of functionalities either in the 2,2′ or 3,3′ positions is then easily achieved in high yields via the use of BOC protecting groups, functioning orthogonally to TBS.