Brown Allylation: Application to the Synthesis of Natural Products
European Journal of Organic Chemistry , Volume 2021, pp 3214-3222; doi:10.1002/ejoc.202100258
Abstract: Asymmetric allylation represents an important reaction applied in the natural product synthesis. The stereoselective introduction of an allyl group allows to obtain versatile chiral building blocks, which may further undergo various transformations due to the presence of the carbon‐carbon double bond. In this review, we address the Brown allylation, which involves the conversion of aldehydes into homoallylic alcohols using B‐allyldiisopinocampheylborane as a chiral reagent. We provide a comprehensive overview of the reaction and highlight its application in the synthesis of natural products, while assessing its performance in comparison to other approaches. The total of 17 syntheses have been described, including the synthesis of biologically active macrolides Disciformycin B, Biselyngbyolide B, Peloruside A and Gliomasolide A, bis‐piperidine alkaloid (–)‐Anaferine and Dysoxylactam A.
Keywords: Brown allylation / asymmetric allylation / synthesis of natural products / B-allyldiisopinocampheylborane
Scifeed alert for new publicationsNever miss any articles matching your research from any publisher
- Get alerts for new papers matching your research
- Find out the new papers from selected authors
- Updated daily for 49'000+ journals and 6000+ publishers
- Define your Scifeed now
Click here to see the statistics on "European Journal of Organic Chemistry" .