Chiral Brønsted Acid Catalyzed Enantioselective Aza-Diels-Alder Reaction of Brassard's Diene with Imines

Brønsted, Brassard, Diels, and Alder: Aldimines 1 undergo aza‐Diels–Alder reactions with Brassard's diene 2 in the presence of a chiral cyclic phosphate pyridinium salt 4 as a chiral Brønsted acid to give α,β‐unsaturated δ‐lactams 3 with excellent enantioselectivity.

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Bibliographic Details
Published inAngewandte Chemie (International ed.) Vol. 45; no. 29; pp. 4796 - 4798
Main Authors Itoh, Junji, Fuchibe, Kohei, Akiyama, Takahiko
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 17.07.2006
WILEY‐VCH Verlag
Wiley
Subjects
Acids - chemistry
asymmetric synthesis
Aza Compounds - chemistry
aza-Diels-Alder reaction
Brønsted acids
Catalysis
Chemistry
Chemistry, Multidisciplinary
Cyclization
enantioselectivity
Imines - chemistry
Models, Molecular
Molecular Structure
organocatalysis
Physical Sciences
Science & Technology
Stereoisomerism
enantioselectivity
ACTIVATION
1,3-DICARBONYL COMPOUNDS
TRANSFER HYDROGENATION
CARBONYL-COMPOUNDS
DIENOPHILES
organocatalysis
CYCLOADDITION
asymmetric synthesis
aza-Diels-Alder reaction
MANNICH REACTIONS
ASYMMETRIC ORGANOCATALYSIS
ZIRCONIUM CATALYST
Bronsted acids
EFFICIENT
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Summary:Brønsted, Brassard, Diels, and Alder: Aldimines 1 undergo aza‐Diels–Alder reactions with Brassard's diene 2 in the presence of a chiral cyclic phosphate pyridinium salt 4 as a chiral Brønsted acid to give α,β‐unsaturated δ‐lactams 3 with excellent enantioselectivity.
Bibliography:istex:17885EE30603588D293DE014EEC7795558E6CB5A
ark:/67375/WNG-BDRBRKGK-X
We thank Professor Youichi Ishii and Dr. Yoshiaki Tanabe (Chuo University, Tokyo, Japan) for the X-ray structural determination. This work was partially supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Science, Sports, Culture, and Technology, Japan. J.I. is grateful for a JSPS Research Fellowship for Young Scientists.
ArticleID:ANIE200601345
We thank Professor Youichi Ishii and Dr. Yoshiaki Tanabe (Chuo University, Tokyo, Japan) for the X‐ray structural determination. This work was partially supported by a Grant‐in‐Aid for Scientific Research from the Ministry of Education, Science, Sports, Culture, and Technology, Japan. J.I. is grateful for a JSPS Research Fellowship for Young Scientists.
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SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200601345