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Synthesis of Bifunctional Allylic Compounds by Using Cyclopropenes as Functionalized Allyl Equivalents
Author(s) -
Mata Sergio,
López Luis A.,
Vicente Rubén
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201806961
Subject(s) - allylic rearrangement , atom economy , bifunctional , chemistry , regioselectivity , carbene , intramolecular force , combinatorial chemistry , catalysis , medicinal chemistry , organic chemistry
Abstract The synthesis of uncommon bifunctional allylic derivatives bearing a silane and an alcohol within the same allylic framework is reported. This method relies on the coupling of hydrosilanes with substituted and functionalized cyclopropenes, which deliver the allyl fragment. Rhodium(II) catalysts provide regioselective access to vinyl carbene intermediates, which easily undergo Si−H bond insertions. The transformation occurs with complete atom economy and shows a remarkably broad scope, including a intramolecular version for the synthesis of cyclic O−Si‐linked compounds as well as the synthesis of the corresponding allyl amines.