Department of Chemistry, School of Chemistry, Chemical Engineering and Life Science , Wuhan University of Technology , Wuhan 430070 , P.R. China.
Org Lett. 2018 May 4;20(9):2585-2589. doi: 10.1021/acs.orglett.8b00721. Epub 2018 Apr 13.
A three-component Petasis-type gem-difluoroallylation reaction of using pinacol gem-difluoroallylboronates, aldehydes or isatin, and β-amino alcohols enabled by the neighboring hydroxyl group in amine is reported, affording various racemic and chiral gem-difluorohomoallylamine derivatives with good to excellent results. Based on the control experiment and stereochemistry of the product, a proposed reaction pathway is illustrated to clarify the origin of regio- and stereoselectivity under protic solvent conditions.
本文报道了一种三组分 Petasis 型 gem-二氟烯丙基化反应，使用频哪醇 gem-二氟烯丙基硼酸酯、醛或色胺以及β-氨基醇，通过胺中的邻羟基基团实现，得到了各种外消旋和手性 gem-二氟同型烯丙胺衍生物，产率良好到优秀。基于对照实验和产物的立体化学，提出了一种反应途径，以阐明在质子溶剂条件下区域和立体选择性的起源。
