School of Pharmaceutical Sciences, Shandong University , Jinan 250012, China.
School of Chemistry and Chemical Engineering, Shandong University , Jinan 250100, China.
Org Lett. 2017 Apr 21;19(8):2146-2149. doi: 10.1021/acs.orglett.7b00787. Epub 2017 Apr 12.
A regio- and diastereoselective cross-dehydrogenative coupling of N-carbamoyl tetrahydropyridines with a variety of 1,3-dicarbonyl compounds is described. The method exhibits good functional group tolerance, diastereoselectively generating cis-2,6- or cis-2,4-substituted tetrahydropyridines by using different types of 1,3-dicarbonyls. Moreover, a two-step sequence involving diastereoselective cross-dehydrogenative coupling followed by epimerization was also developed, allowing facile access to trans-2,6-substituted tetrahydropyridines as single isomers. Applications in natural product synthesis and divergent analogue preparation were further demonstrated.
本文描述了 N-氨甲酰基四氢吡啶与各种 1,3-二羰基化合物的区域和立体选择性交叉脱氢偶联。该方法具有良好的官能团耐受性，通过使用不同类型的 1,3-二羰基化合物，立体选择性地生成顺式-2,6-或顺式-2,4-取代的四氢吡啶。此外，还开发了两步序列，包括立体选择性交叉脱氢偶联和随后的差向异构化，可轻松获得作为单一异构体的反式-2,6-取代的四氢吡啶。进一步展示了在天然产物合成和发散类似物制备中的应用。
