TY - CHAP
T1 - Hetero-Diels-Alder Reactions
AU - Ishihara, K.
AU - Sakakura, A.
N1 - Funding Information:
Kazuaki Ishihara obtained his PhD from Nagoya University in 1991 under the direction of Prof. Hisashi Yamamoto. He had the opportunity to work under the direction 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. E. J. 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 an 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 & 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), the Mukaiyama Award (2009), and the Inoue Prize for Science (2011). His research interests include asymmetric catalysis, biomimetic catalysis, green catalysis, supramolecular catalysts based on acid–base combination chemistry, and so on.
PY - 2014/2
Y1 - 2014/2
N2 - Diels-Alder reactions that include a heteroatom in the dienes or dienophiles are called 'hetero-Diels-Alder reactions.' Hetero-Diels-Alder reactions are highly useful for the stereoselective construction of a variety of heterocycles, and have been extensively used in the syntheses of bioactive natural and synthetic compounds. Over the past 20 years, various diastereo- and enantioselective hetero-Diels-Alder reactions have been developed. This chapter describes recent significant advancements in this field since the publication of the first edition of Comprehensive of Organic Synthesis in 1991. First, we summarize enantioselective hetero-Diels-Alder reactions of carbonyl compounds, which are promoted by chiral Lewis acid catalysts or organocatalysts. Next, we describe representative examples of asymmetric aza-Diels-Alder reactions. We also summarize recent significant advances in the stereoselective hetero-Diels-Alder reactions of other dienes and dienophiles such as nitroso compounds. Finally, we present representative studies on the biomimetic synthesis of bioactive natural products using hetero-Diels-Alder reactions.
AB - Diels-Alder reactions that include a heteroatom in the dienes or dienophiles are called 'hetero-Diels-Alder reactions.' Hetero-Diels-Alder reactions are highly useful for the stereoselective construction of a variety of heterocycles, and have been extensively used in the syntheses of bioactive natural and synthetic compounds. Over the past 20 years, various diastereo- and enantioselective hetero-Diels-Alder reactions have been developed. This chapter describes recent significant advancements in this field since the publication of the first edition of Comprehensive of Organic Synthesis in 1991. First, we summarize enantioselective hetero-Diels-Alder reactions of carbonyl compounds, which are promoted by chiral Lewis acid catalysts or organocatalysts. Next, we describe representative examples of asymmetric aza-Diels-Alder reactions. We also summarize recent significant advances in the stereoselective hetero-Diels-Alder reactions of other dienes and dienophiles such as nitroso compounds. Finally, we present representative studies on the biomimetic synthesis of bioactive natural products using hetero-Diels-Alder reactions.
KW - Asymmetric catalysis
KW - Biomimetic synthesis
KW - Diastereoselectivity
KW - Enantioselectivity
KW - Hetero-Diels-Alder reaction
KW - Heterodienes
KW - Heterodienophiles
KW - Lewis acid catalysts
KW - Nitroso compounds
KW - Organocatalysts
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U2 - 10.1016/B978-0-08-097742-3.00510-3
DO - 10.1016/B978-0-08-097742-3.00510-3
M3 - Chapter
AN - SCOPUS:84903497562
SN - 9780080977430
VL - 5
SP - 409
EP - 465
BT - Combining C-C π-Bonds
PB - Elsevier Ltd
ER -