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Highly Stereoselective Cyclopropanation of α,β‐Unsaturated Carbonyl Compounds with Methyl (Diazoacetoxy)acetate Catalyzed by a Chiral Ruthenium(II) Complex
Author(s) -
Chanthamath Soda,
Takaki Suguru,
Shibatomi Kazutaka,
Iwasa Seiji
Publication year - 2013
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.201300468
Subject(s) - cyclopropanation , cyclopropane , stereoselectivity , enantioselective synthesis , oxindole , ruthenium , chemistry , catalysis , stereochemistry , organic chemistry , medicinal chemistry , ring (chemistry)
Tantalizing triangles : The title reaction gives bicarbonyl cyclopropane products that can lead to versatile intermediates with high yields and stereoselectivities. This system was also applied to the enantioselective total synthesis of spiro cyclopropane oxindole, an HIV‐1 nonnucleoside reverse transcriptase inhibitor.