Stereoselective synthesis of 3-aminoindan-1-ones and subsequent incorporation into HIV-1 protease inhibitors

被引：21

作者：

Arefalk, A ^{[1
]}

Wannberg, J ^{[1
]}

Larhed, M ^{[1
]}

Hallberg, A ^{[1
]}

机构：

[1] Uppsala Univ, Dept Med Chem, BMC, SE-75123 Uppsala, Sweden

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 03期

关键词：

D O I：

10.1021/jo0521504

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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. © 2006 American Chemical Society.

引用

页码：1265 / 1268

页数：4

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