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Brown Allylation: Application to the Synthesis of Natural Products
Author(s) -
Boiarska Zlata,
Braga Tommaso,
Silvani Alessandra,
Passarella Daniele
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100258
Subject(s) - chemistry , piperidine , natural product , total synthesis , stereoselectivity , reagent , enantioselective synthesis , double bond , combinatorial chemistry , organic chemistry , stereochemistry , catalysis
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.