NH₄HF₂作为一种用于通过串联脱保护/螺缩酮化过程合成高官能化螺缩酮的选择性TBS去除试剂。

NH₄HF₂ as a selective TBS-removal reagent for the synthesis of highly functionalized spiroketal via tandem deprotection/spiroketalization procedure.

作者信息

Lu Hui, Zhang Fu-Min, Pan Jin-Long, Chen Tao, Li Yi-Fan

机构信息

State Key Laboratory of Applied Organic Chemistry and Department of Chemistry Lanzhou University , Lanzhou 730000, P. R. China.

出版信息

J Org Chem. 2014 Jan 17;79(2):546-58. doi: 10.1021/jo402167q. Epub 2013 Dec 24.

DOI:10.1021/jo402167q

PMID:24328167

Abstract

NH4HF2 has been used for the first time to selectively remove the TBS protecting groups from diol ketone precursors in the synthesis of highly functionalized spiroketals. This method allows the synthesis of [5,6], [6,6], and [6,7] spiroketal skeletons, as well as benzannulated spiroketal with retention of acid-sensitive groups. In this way, spiroketals can be synthesized with diverse substituent groups in the skeleton or on side chains. To demonstrate the utility of this methodology, the diverse transformations of highly functionalized spiroketal 3f were also investigated.

摘要

在高官能化螺缩酮的合成中，首次使用NH4HF2从二醇酮前体中选择性去除叔丁基二甲基硅烷基（TBS）保护基团。该方法能够合成[5,6]、[6,6]和[6,7]螺缩酮骨架，以及保留酸敏感基团的苯并稠合螺缩酮。通过这种方式，可以合成骨架或侧链上具有不同取代基的螺缩酮。为了证明该方法的实用性，还研究了高官能化螺缩酮3f的各种转化反应。