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Highly Regio‐, Diastereo‐, and Enantioselective [2+2+2] Cycloaddition of 1,6‐Enynes with Electron‐Deficient Ketones Catalyzed by a Cationic Rh I /H 8 ‐binap Complex
Author(s) -
Tanaka Ken,
Otake Yousuke,
Sagae Hiromi,
Noguchi Keiichi,
Hirano Masao
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.200704758
Subject(s) - cationic polymerization , enantioselective synthesis , catalysis , aryl , cycloaddition , amide , chemistry , binap , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry , alkyl
Two quaternary carbon centers are created in the title reaction to form fused dihydropyrans (see scheme). The same catalyst promotes the ortho functionalization of aryl ketones with 1,6‐enynes with excellent regio‐ and enantioselectivity. Z=amide, C(CO 2 Me) 2 , O; E=CO 2 Et, Ac; R 1 =Me, aryl, CO 2 Me; R 2 =Me; R 3 =Me, CO 2 Et.