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An Ethynyl-Substituted 1,5,7-Trimethyl-3-azabicyclo[3.3.1]nonan-2-one as a Versatile Precursor for Chiral Templates and Chiral Photocatalysts
Synlett ( IF 1.7 ) Pub Date : 2010-05-06 , DOI: 10.1055/s-0029-1219920
Thorsten Bach , Felix Voss

The title compound was synthesized and separated into its enantiomers. The enantiomerically pure alkyne was ligated to several aryl azides and aryl halides. The resulting 7-substituted 1,5,7-trimethyl-3-azabicyclo[3.3.1]nonan-2-ones were used either as chiral templates in the intramolecular [2+2] photocycloaddition of 4-allyloxyquinolone (up to 72% ee) or as a chiral photocatalyst for the intramolecular [2+2] photocycloaddition of 4-(3-butenyl-oxy)quinolone (up to 79% ee with 10 mol% catalyst).

中文翻译:

乙炔基取代的 1,5,7-Trimethyl-3-azabicyclo[3.3.1]nonan-2-one 作为手性模板和手性光催化剂的通用前体

合成标题化合物并分离为其对映异构体。对映体纯炔烃连接到几个芳基叠氮化物和芳基卤化物。所得的 7-取代 1,5,7-三甲基-3-氮杂双环 [3.3.1]nonan-2-ones 用作 4-烯丙氧基喹诺酮分子内 [2+2] 光环加成的手性模板(高达 72% ee) 或作为手性光催化剂用于 4-(3-丁烯基-氧基) 喹诺酮的分子内 [2+2] 光环加成反应(使用 10 mol% 催化剂时可达 79% ee)。
更新日期:2010-05-06
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