N-Heterocyclic Carbene/Lewis Acid Dual Catalysis for the Divergent Construction of Enantiopure Bridged Lactones and Fused Indenes

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• 作者：Zhan-Yong Wang ; Ya-Li Ding ; Shi-Ning Li ; Ying Cheng
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：December 2, 2016
• 年：2016
• 卷：81
• 期：23
• 页码：11871-11881
• 全文大小：490K
• ISSN：1520-6904

文摘

The chiral triazole carbene and Ti(OPr-i)₄ cocatalyzed reaction between α,β-unsaturated aldehydes and 2-(aroylvinyl)benzaldehydes was systematically studied. A divergence in reaction pathways was observed under different reaction conditions. In benzene solvent and at ambient temperature, the reaction produced 4,5-dihydro-1,4-methanobenzo[c]oxepin-3-ones, the bridged caprolactones, as the major products in moderate yields with excellent enantioselectivity. The same reaction in dichloroethane and at 50 °C, however, gave 2,8-dihydrocyclopenta[a]indenes as the major products in most cases. The application of the method developed was demonstrated by the transformation of the bridged lactone products into enantiopure 4-hydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acids.