Abstract
The asymmetric Diels-Alder reaction is one of the most powerful organic transformations and is a versatile tool for the synthesis of many bioactive natural products. The asymmetric hetero-Diels-Alder reactions of carbonyl compounds and imino compounds are also among the most powerful methodologies for the construction of optically active heterocycles, and there are extensive applications of these reactions in the synthesis of bioactive natural and unnatural compounds. In addition to conventional Lewis acid catalysis, organocatalysis has been successfully applied to the enantioselective Diels-Alder reaction. Through the use of chiral secondary and primary organoammonium salt catalysts and hydrogen-bonding catalysts, the enantioselective Diels-Alder reaction of dienes with α,. β-unsaturated carbonyl compounds can be promoted. Chiral secondary and primary organoammonium salt catalysts activate α,. β-unsaturated carbonyl compounds via the formation of an iminium cation intermediate, whereas chiral hydrogen-bonding catalysts activate these compounds via coordination of the carbonyl group.
| Original language | English |
|---|---|
| Title of host publication | Comprehensive Chirality |
| Publisher | Elsevier Ltd |
| Pages | 264-292 |
| Number of pages | 29 |
| Volume | 6 |
| ISBN (Print) | 9780080951683 |
| DOIs | |
| Publication status | Published - Sep 2012 |
| Externally published | Yes |
Fingerprint
Keywords
- Cinchona alkaloid
- Enanine
- Iminium ion
- LUMO-lowering activation
- Phosphoric acid
ASJC Scopus subject areas
- Chemistry(all)
Cite this
6.10 C-C Bond Formation : Diels-Alder Reaction. / Ishihara, K.; Sakakura, Akira.
Comprehensive Chirality. Vol. 6 Elsevier Ltd, 2012. p. 264-292.Research output: Chapter in Book/Report/Conference proceeding › Chapter
}
TY - CHAP
T1 - 6.10 C-C Bond Formation
T2 - Diels-Alder Reaction
AU - Ishihara, K.
AU - Sakakura, Akira
PY - 2012/9
Y1 - 2012/9
N2 - The asymmetric Diels-Alder reaction is one of the most powerful organic transformations and is a versatile tool for the synthesis of many bioactive natural products. The asymmetric hetero-Diels-Alder reactions of carbonyl compounds and imino compounds are also among the most powerful methodologies for the construction of optically active heterocycles, and there are extensive applications of these reactions in the synthesis of bioactive natural and unnatural compounds. In addition to conventional Lewis acid catalysis, organocatalysis has been successfully applied to the enantioselective Diels-Alder reaction. Through the use of chiral secondary and primary organoammonium salt catalysts and hydrogen-bonding catalysts, the enantioselective Diels-Alder reaction of dienes with α,. β-unsaturated carbonyl compounds can be promoted. Chiral secondary and primary organoammonium salt catalysts activate α,. β-unsaturated carbonyl compounds via the formation of an iminium cation intermediate, whereas chiral hydrogen-bonding catalysts activate these compounds via coordination of the carbonyl group.
AB - The asymmetric Diels-Alder reaction is one of the most powerful organic transformations and is a versatile tool for the synthesis of many bioactive natural products. The asymmetric hetero-Diels-Alder reactions of carbonyl compounds and imino compounds are also among the most powerful methodologies for the construction of optically active heterocycles, and there are extensive applications of these reactions in the synthesis of bioactive natural and unnatural compounds. In addition to conventional Lewis acid catalysis, organocatalysis has been successfully applied to the enantioselective Diels-Alder reaction. Through the use of chiral secondary and primary organoammonium salt catalysts and hydrogen-bonding catalysts, the enantioselective Diels-Alder reaction of dienes with α,. β-unsaturated carbonyl compounds can be promoted. Chiral secondary and primary organoammonium salt catalysts activate α,. β-unsaturated carbonyl compounds via the formation of an iminium cation intermediate, whereas chiral hydrogen-bonding catalysts activate these compounds via coordination of the carbonyl group.
KW - Cinchona alkaloid
KW - Enanine
KW - Iminium ion
KW - LUMO-lowering activation
KW - Phosphoric acid
UR - http://www.scopus.com/inward/record.url?scp=84902430637&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84902430637&partnerID=8YFLogxK
U2 - 10.1016/B978-0-08-095167-6.00610-8
DO - 10.1016/B978-0-08-095167-6.00610-8
M3 - Chapter
AN - SCOPUS:84902430637
SN - 9780080951683
VL - 6
SP - 264
EP - 292
BT - Comprehensive Chirality
PB - Elsevier Ltd
ER -