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Nickel( 0 )‐Catalyzed Three‐Component Connection Reaction of Dimethylzinc, 1,3‐Dienes, and Carbonyl Compounds
Author(s) -
Kimura Masanari,
Matsuo Shintaro,
Shibata Kazufumi,
Tamaru Yoshinao
Publication year - 1999
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/(sici)1521-3773(19991115)38:22<3386::aid-anie3386>3.0.co;2-w
Subject(s) - dimethylzinc , chemistry , steric effects , catalysis , acetone , adduct , carbonyl group , medicinal chemistry , nickel , organic chemistry
Linear 1:1:1 coupling of dimethylzinc, 1,3‐dienes, and carbonyl compounds in this order is facilitated by catalytic amounts of [Ni(acac) 2 ] to give ( E )‐3‐hexen‐1‐ols in good yields under mild conditions [Eq. (a)]. Increasing steric hindrance at the carbonyl group favors formation of the 1:2:1 adduct, and this is the sole product when the carbonyl compound is acetone. acac=acetylacetonate.