TY - CHAP
T1 - 6.10 C-C Bond Formation
T2 - Diels-Alder Reaction
AU - Ishihara, K.
AU - Sakakura, A.
N1 - Funding Information:
Kazuaki Ishihara received his PhD from Nagoya University in 1991 under the supervision of Prof. Hisashi Yamamoto. He had the opportunity to work under the supervision of Prof. Clayton H Heathcock at the University of California, Berkeley, as a visiting graduate student in 1988. He was a JSPS Fellow under the Japanese Junior Scientists Program from 1989 to 1991. After completing his postdoctoral studies with Prof. EJ Corey at Harvard University, he returned to Japan and joined Prof. H Yamamoto's group at Nagoya University as an assistant professor in 1992, and became associate professor in 1997. In 2002, he was appointed to his current position as a full professor at Nagoya University. He has received the Inoue Research Award for Young Scientists (1994), the Chemical Society of Japan Award for Young Chemists (1996), the Thieme Chemistry Journal Award (2001), the Green and Sustainable Chemistry Award from the Ministry of Education, Culture, Sports, Science, and Technology (2003), the JSPS Prize (2005), the BCSJ Award (2005), the Japan IBM Science Prize (2007), and the Mukaiyama Award (2009). His research interests include asymmetric catalysis, biomimetic catalysis induced by artificial enzymes, dehydrative condensation catalysis, and acid–base combination chemistry.
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
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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 - Synthetic Methods V - Organocatalysis
PB - Elsevier Ltd
ER -