Stereocontrol in a combined allylic azide rearrangement and intramolecular Schmidt reaction.

Stereocontrol in a combined allylic azide rearrangement and intramolecular Schmidt reaction.
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DOI:
10.1021/ja300369c
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发表时间:
2012-04-18
影响因子:
15
通讯作者:
Aube, Jeffrey
Aube, Jeffrey
中科院分区:
化学1区
文献类型:
--
作者:
Liu, Ruzhang;Gutierrez, Osvaldo;Tantillo, Dean J.;Aube, Jeffrey

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Preequilibration of an interconverting set of isomeric allylic azides is coupled with an intramolecular Schmidt reaction to stereoselectively afford substituted lactams. The effect of substitution and a preliminary mechanistic study are reported. The synthetic potential of this method is demonstrated in the context of an enantioselective synthesis of an advanced intermediate toward pinnaic acid.
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