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Nickel‐Catalyzed Reductive Cyclization of Unactivated 1,6‐Enynes in the Presence of Organozinc Reagents
Author(s) -
Chen Mao,
Weng Yue,
Guo Mian,
Zhang Hua,
Lei Aiwen
Publication year - 2008
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.200704452
Subject(s) - tetrahydrofuran , catalysis , nickel , reagent , chemistry , stereoselectivity , hydrolysis , aryl , alkyl , pyrrolidine , organic chemistry , medicinal chemistry , combinatorial chemistry , solvent
Pyrrolidine and tetrahydrofuran derivatives were synthesized in a highly stereoselective manner through the Ni‐catalyzed reduction of the title compounds under mild conditions (see scheme). The product of cyclization is initially associated with both a Ni and a Zn species, the removal of which by elimination and hydrolysis corresponds to the formal incorporation of dihydrogen. acac=acetylacetonate; R=alkyl, aryl; X=N, O.