Synthesis of the PMB Ether of 5,6-Epoxyisoprostane E2 through Aldol Reaction of the α-Bromocyclopentanone
摘要:
5,6-Epoxyisoprostane E2 was synthesized via bromohydrination of the cyclopentene and aldol reaction of the alpha-bromocyclopentanone with the epoxyaldehyde. High regioselectivity in the bromohydrination was attained with recrystallized NBS and pyridine in aqueous DMSO. The enolate for the aldol reaction was generated by adding t-BuLi to the mixture of the a-bromocyclopentanone and ZnI2. This aldol protocol was applied successfully to several cyclopentanones and aldehydes.
Redox-Neutral Ni-Catalyzed sp<sup>3</sup> C–H Alkylation of α-Olefins with Unactivated Alkyl Bromides
作者:Mikkel B. Buendia、Bradley Higginson、Søren Kegnæs、Søren Kramer、Ruben Martin
DOI:10.1021/acscatal.2c01057
日期:2022.4.1
A light-induced redox-neutral Ni-catalyzed sp3 C–H alkylation of unactivatedalkenes with alkyl bromides possessing β-hydrogens is described herein. The method is distinguished by its simplicity, wide scope, and exquisite regio- and chemoselectivity profile, thus offering an entry point to forge sp3–sp3 architectures.