Amino Amide Organocatalysts for Asymmetric Michael Addition of β-Keto Esters with β-Nitroolefins

Asymmetric Michael addition of β-keto esters with trans-β-nitroolefins using chiral amino amide organocatalyst was tried and afforded synthetically useful chiral Michael adducts in both excellent chemical yields (up to 99%) and stereoselectivities (up to dr. 99:1, up to 98% ee).

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Bibliographic Details
Published inBulletin of the Chemical Society of Japan Vol. 92; no. 3; pp. 696 - 701
Main Authors Owolabi, Isiaka Alade, Chennapuram, Madhu, Seki, Chigusa, Okuyama, Yuko, Kwon, Eunsang, Uwai, Koji, Tokiwa, Michio, Takeshita, Mitsuhiro, Nakano, Hiroto
Format Journal Article
LanguageEnglish
Published TOKYO The Chemical Society of Japan 2019
Chemical Soc Japan
Chemical Society of Japan
Subjects
Adducts
Chemistry
Chemistry, Multidisciplinary
Esters
Organic chemistry
Physical Sciences
Science & Technology
Michael addition
Organocatalyst
Amino amide
ALCOHOL ORGANOCATALYST
EFFICIENT ORGANOCATALYSTS
1,3-DICARBONYL COMPOUNDS
ADJACENT QUATERNARY
NATURAL-PRODUCTS
QUATERNARY STEREOCENTERS
CHIRAL 2-AMINOBENZIMIDAZOLES
ENANTIOSELECTIVE CONJUGATE ADDITION
DIELS-ALDER REACTION
TERTIARY STEREOCENTERS
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ISSN0009-2673
1348-0634
DOI10.1246/bcsj.20180302

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Summary:Asymmetric Michael addition of β-keto esters with trans-β-nitroolefins using chiral amino amide organocatalyst was tried and afforded synthetically useful chiral Michael adducts in both excellent chemical yields (up to 99%) and stereoselectivities (up to dr. 99:1, up to 98% ee).
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.20180302