Stereoselective synthesis of 3-aminoindan-1-ones and subsequent incorporation into HIV-1 protease inhibitors
Stereoselective synthesis of 3-aminoindan-1-ones and subsequent incorporation into HIV-1 protease inhibitors
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DOI：
10.1021/jo0521504
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发表时间：
2006-02-03
影响因子：
3.6
通讯作者：
Hallberg, A
中科院分区：
文献类型：
--
作者：
Arefalk, A;Wannberg, J;Hallberg, A
提出了以水杨基亚胺三酸酯和乙二醇乙烯醚为原料立体选择性合成3-氨基氨基酸-1- 1的新方法。反应顺序从区域选择性Heck反应开始，然后是立体选择性Lewis酸介导的环化。亚胺的酸性裂解产生了纯的(R)-和(S)-3-氨基氨基酸-1，它们被成功分离并结合到活性HIV-1蛋白酶抑制剂中。
A new method for the stereoselective synthesis of 3-aminoindan-1-ones from triflates of salicylic sulfinyl imines and ethylene glycol vinyl ether has been developed. The reaction sequence starts with a regioselective Heck reaction followed by stereoselective Lewis acid mediated annulation. Acidic cleavage of the sulfinamides produced pure (R)- and (S)-3-aminoindan-1-ones, which were successfully isolated and incorporated into active HIV-1 protease inhibitors.