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Brown Allylation: Application to the Synthesis of Natural Products

Zlata Boiarska, Tommaso Braga, Alessandra Silvani,
Published: 6 May 2021
 by  Wiley
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

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