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Highly Regio‐ and Stereoselective Cycloreductions of 1,6‐ and 1,7‐Enynes Activated with a Carbonyl Functionality
Author(s) -
Oh Chang Ho,
Jung Hyung Hoon,
Kim Joo Sung,
Cho Seung Woo
Publication year - 2000
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(20000218)39:4<752::aid-anie752>3.0.co;2-i
Subject(s) - stereoselectivity , chemistry , formic acid , carbonyl group , catalysis , diene , enyne , palladium catalyst , palladium , organic chemistry , medicinal chemistry , stereochemistry , natural rubber
An up to 99:1 stereochemical excess of 3 is reported for the cycloreduction of the title enynes 1 using a palladium‐based catalyst and formic acid. The two‐step process involves β ‐elimination of the coordinated enyne to form diene 2 , followed by 2 recoordinating and the regio‐ and stereoselective reduction to produce the γ , δ ‐unsaturated carbonyl product 3 . R=carbonyl group.