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Modular Synthesis of a Versatile Double‐Allylation Reagent for Complex Diol Synthesis
Author(s) -
Dorn Stanna K.,
Tharp Annika E.,
Brown M. Kevin
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202103435
Subject(s) - reagent , modular design , modularity (biology) , diol , enantioselective synthesis , combinatorial chemistry , chemistry , computer science , catalysis , organic chemistry , programming language , biology , genetics
Double‐allylation reagents allow for the construction of highly complex molecules in an expedient fashion. We have developed an efficient, modular, and enantioselective approach towards accessing novel variants of these reagents through Cu/Pd‐catalyzed alkenylboration of alkenylboron derivatives. Importantly, we demonstrate novel use of an allylBdan reagent directly in a stereocontrolled allylation without initial deprotection to the boronic ester. These allylation products are employed in a second intermolecular allylation to access complex diol motifs, which has yet to be shown with these types of double‐allylation reagents. Overall, the modularity of this approach and the ease in which complex structural motifs can be accessed in a rapid manner signify the importance and utility of this method.