TY - CHAP
T1 - Intermolecular Diels-Alder Reactions
AU - Ishihara, K.
AU - Sakakura, A.
N1 - Funding Information:
Kazuaki Ishihara received his PhD from Nagoya University, Japan 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, USA 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, etc.
PY - 2014/2
Y1 - 2014/2
N2 - The Diels-Alder reaction is one of the most powerful carbon-carbon bond-forming reactions and is a versatile tool for the synthesis of many bioactive natural products. Since it was first shown that the Diels-Alder reaction could be effectively promoted by Lewis acids, stereoselective versions have been extensively investigated. This chapter focuses on representative achievements in this field after publication of the first edition of Comprehensive of Organic Synthesis in 1991. The authors summarize chiral Lewis acid catalysis, including chiral boron(III), copper(II), and other metal complexes, for use in diastereo- and enantioselective Diels-Alder reactions. Next, recent significant advances in asymmetric organocatalysis, including organoammonium catalysis and hydrogen-bonding catalysis, are described. Examples of natural product syntheses based on the asymmetric Diels-Alder reaction using Lewis acid catalysts or organocatalysts are also described. Finally, representative studies on the biomimetic synthesis of natural compounds using intermolecular Diels-Alder reactions are shown.
AB - The Diels-Alder reaction is one of the most powerful carbon-carbon bond-forming reactions and is a versatile tool for the synthesis of many bioactive natural products. Since it was first shown that the Diels-Alder reaction could be effectively promoted by Lewis acids, stereoselective versions have been extensively investigated. This chapter focuses on representative achievements in this field after publication of the first edition of Comprehensive of Organic Synthesis in 1991. The authors summarize chiral Lewis acid catalysis, including chiral boron(III), copper(II), and other metal complexes, for use in diastereo- and enantioselective Diels-Alder reactions. Next, recent significant advances in asymmetric organocatalysis, including organoammonium catalysis and hydrogen-bonding catalysis, are described. Examples of natural product syntheses based on the asymmetric Diels-Alder reaction using Lewis acid catalysts or organocatalysts are also described. Finally, representative studies on the biomimetic synthesis of natural compounds using intermolecular Diels-Alder reactions are shown.
KW - Asymmetric catalysis
KW - Biomimetic synthesis
KW - Cycloaddition
KW - Diastereoselectivity
KW - Diels-Alder reaction
KW - Dienes
KW - Dienophiles
KW - Enantioselectivity
KW - Lewis acid catalysts
KW - Organocatalysts
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U2 - 10.1016/B978-0-08-097742-3.00509-7
DO - 10.1016/B978-0-08-097742-3.00509-7
M3 - Chapter
AN - SCOPUS:84903496122
SN - 9780080977430
VL - 5
SP - 351
EP - 408
BT - Combining C-C π-Bonds
PB - Elsevier Ltd
ER -