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An N-Heterocyclic Carbene-Mediated, Enantioselective and Multicatalytic Strategy to Access Dihydropyranones in a Sequential Three-Component One-Pot Reaction
Organic Letters ( IF 5.2 ) Pub Date : 2017-11-08 00:00:00 , DOI: 10.1021/acs.orglett.7b02889
Patrick J. W. Fuchs 1 , Kirsten Zeitler 1
Affiliation  

The multicatalytic generation of 3,5,6-trisubstituted 3,4-dihydropyranones with high enantioselectivity using a highly convergent strategy starting from commercially available precursors is reported. The operationally simple three-step, one-pot protocol merges H-bond and NHC catalysis to provide crucial, reactive β-unsubstituted enones from nitroalkenes as latent 1,2-biselectrophiles. These intermediates are directly funneled into a further NHC-catalyzed formal hetero-Diels–Alder reaction to deliver manifold chiral C(4)-unsubstituted dihydropyranones (typical ee >98%), allowing aliphatic and heteroaromatic substituents and hence expanding the scope of this Michael addition/lactonization.

中文翻译:

一个ñ N-杂环卡宾介导的,对映选择性和Multicatalytic策略访问Dihydropyranones在连续三组分一锅反应

据报道,从市场上可买到的前体开始,采用高度收敛的策略,以高对映选择性多催化生成3,5,6-三取代的3,4-二氢吡喃酮。该操作简单的三步一锅操作方案将H键和NHC催化合并,从硝基烯烃中作为潜在的1,2-双亲电子试剂提供了关键的,反应性的β-未取代的烯酮。这些中间体直接漏斗到进一步的NHC催化的正式杂Diels-Alder反应中,以提供多种手性C(4)-未取代的二氢吡喃酮(典型ee > 98%),允许脂族和杂芳族取代基,因此扩大了该迈克尔加成/内酯化。
更新日期:2017-11-08
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