Enantioselective Total Synthesis of (−)-α-Kainic Acid

An enantioselective total synthesis of (−)-α-kainic acid is described. Key steps are an Ir-catalyzed allylic amination with a propargylic amine to provide an enyne and a diastereoselective intramolecular Pauson−Khand reaction. Subsequent steps involve a Baeyer−Villiger reaction, reduction of the res...

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Bibliographic Details
Published inOrganic letters Vol. 12; no. 5; pp. 1108 - 1111
Main Authors Farwick, Andreas, Helmchen, Günter
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.03.2010
Amer Chemical Soc
Subjects
Amination
Catalysis
Chemistry
Chemistry, Organic
Hydrogenation
Iridium - chemistry
Kainic Acid - chemical synthesis
Kainic Acid - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
Substrate Specificity
PAUSON-KHAND REACTION
(-)-KAINIC ACID
ETHERS
STEREOCONTROLLED TOTAL-SYNTHESIS
RADICAL CYCLIZATION
DIRECT CONVERSION
KAINIC ACID
ALLYLIC AMINATIONS
(+)-ALPHA-ALLOKAINIC ACID
ASYMMETRIC TOTAL-SYNTHESIS
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Summary:An enantioselective total synthesis of (−)-α-kainic acid is described. Key steps are an Ir-catalyzed allylic amination with a propargylic amine to provide an enyne and a diastereoselective intramolecular Pauson−Khand reaction. Subsequent steps involve a Baeyer−Villiger reaction, reduction of the resulting lactone, and direct Jones oxidation of a silyl ether.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol1001076