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Divergent Regioselectivity in the Synthesis of Trisubstituted Allylic Alcohols by Nickel‐ and Ruthenium‐Catalyzed Alkyne Hydrohydroxymethylation with Formaldehyde
Author(s) -
Bausch Cory C.,
Patman Ryan L.,
Breit Bernhard,
Krische Michael J.
Publication year - 2011
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.201101496
Subject(s) - regioselectivity , paraformaldehyde , ruthenium , allylic rearrangement , alkyne , catalysis , chemistry , stereoselectivity , formaldehyde , stoichiometry , nickel , organic chemistry , combinatorial chemistry , medicinal chemistry
Stoichiometric metals banned : Nonsymmetrically disubstituted alkynes were converted into primary trisubstituted allylic alcohols upon exposure to paraformaldehyde in the presence of nickel or ruthenium catalysts, which exhibit complementary regioselectivity and complete stereoselectivity in the absence of exogenous reducing agents (see scheme).