Diastereoselective Synthesis of Complex <i>cis</i>-Hexahydroindanes by Reductive Alkylation
作者:Hilan Z. Kaplan、Victor L. Rendina、Jason S. Kingsbury
DOI:10.1021/jo400670y
日期:2013.5.3
An efficient and operationally simple approach to complex cis-hexahydroindanes is reported. Upon Birch reduction of unprotected, C4-alkylated tetrahydroindanols and electrophilic trapping of the tetrasubstituted enolate, cis-fused products are formed with a new stereogenic quaternary carbon. The reaction is convergent, completely diastereoselective, and shows a broad scope with regard to the electrophile
报道了一种有效且操作简单的方法来制备复杂的顺式六氢茚满。在未保护的,C4-烷基化的四氢吲哚醇的桦木还原反应和四取代的烯醇盐的亲电捕集后,与顺式稠合的产物形成了新的立体异构的季碳。该反应是收敛的,完全非对映选择性的,并且在亲电试剂方面显示出广阔的范围。