Efficient synthesis of substituted 3-amino-3,4-dihydropyran-2-ones diastereo and enantioselective tandem Michael addition and lactonization between alpha,beta-unsaturated ketones and glycine-derived silyl enolates using a chiral quaternary ammonium phenoxide

Chiral, quaternary ammonium phenoxides are readily prepared from commercially available cinchona alkaloids and are employed as useful new asymmetric organocatalysts. The cinchonidine-derived catalyst is highly effective on Michael addition and successive lactonization between glycine-derived silyl e...

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Bibliographic Details
Published inHeterocycles Vol. 72; pp. 553 - 565
Main Authors Nagao, Hitoshi, Yamane, Yoshinobu, Mukaiyama, Teruaki
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 13.04.2007
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Michael addition
ROUTE
AMINES
ACIDS
cinchonidine
3-amino-3,4-dihydropyran-2-one
ammonium phenoxide
organocatalyst
DEPROTECTION
EQUIVALENTS
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Summary:Chiral, quaternary ammonium phenoxides are readily prepared from commercially available cinchona alkaloids and are employed as useful new asymmetric organocatalysts. The cinchonidine-derived catalyst is highly effective on Michael addition and successive lactonization between glycine-derived silyl enolates and alpha,beta-unsaturated ketones. According to this asymmetric reaction, the corresponding 3-amino-3,4-dihydropyran-2-ones are formed in high yields with complete diastereoselectivities and excellent enantioselectivities.
ISSN:0385-5414
1881-0942
DOI:10.3987/com-06-s(k)48