Coluccini Carmine, Castelluccio Antonio, Pasini Dario
Department of Organic Chemistry, University of Pavia, Viale Taramelli 10, Pavia, Italy.
J Org Chem. 2008 Jun 6;73(11):4237-40. doi: 10.1021/jo800315s. Epub 2008 Apr 29.
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.
通过对空间位阻较小的外部3,3'苄基位置进行叔丁基二甲基硅基（TBS）保护，实现了在光学活性联萘骨架上邻位酚醇和苄醇的高效化学选择性分化。然后，通过使用与TBS正交的叔丁氧羰基（BOC）保护基团，很容易以高产率对2,2'或3,3'位置的官能团进行进一步操作。
