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Synthesis of Stereodefined Borylated Dendralenes through Copper‐Catalyzed Allylboration of Alkynes
Author(s) -
RiveraChao Eva,
FañanásMastral Martín
Publication year - 2018
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.201806334
Subject(s) - regioselectivity , chemistry , copper , catalysis , combinatorial chemistry , reactivity (psychology) , boron , organic chemistry , medicine , alternative medicine , pathology
An efficient method to access diversely substituted borylated dendralenes from simple and readily available materials is reported. This method is based on a multicomponent copper‐catalyzed allylboration of alkynes with diboron and a 1,4‐dibromo‐2‐butene which provides bromo‐ and boron‐substituted skipped dienes with a remarkable chemo‐, stereo‐, and regioselectivity. These products can be easily transformed into dendralenic organoboronates, which display an extremely versatile reactivity as demonstrated by novel selective transformations.