Asymmetric Michael Reaction of Malononitrile and α,β-Unsaturated Aldehydes Catalyzed by Diarylprolinol Silyl Ether

Hayashi, Yujiro; Hatano, Yutaro; Mori, Naoki

doi:10.1055/a-1846-5007

Cited by 2 publications

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“…Diarylprolinol silyl ethers, introduced independently by Jørgensen and Hayashi in 2005 [145,146], are unquestionably among the most efficient, versatile, and applied organocatalysts that have been thus far proposed [10,11,147]. Not only are they simply synthesized starting from proline, but they are also general and extremely stereoselective.…”

Section: Diarylprolinol-related Organocatalystsmentioning

confidence: 99%

Recent Advances in Asymmetric Synthesis of Pyrrolidine-Based Organocatalysts and Their Application: A 15-Year Update

2023

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In 1971, chemists from Hoffmann-La Roche and Schering AG independently discovered a new asymmetric intramolecular aldol reaction catalyzed by the natural amino acid proline, a transformation now known as the Hajos–Parrish–Eder–Sauer–Wiechert reaction. These remarkable results remained forgotten until List and Barbas reported in 2000 that L-proline was also able to catalyze intermolecular aldol reactions with non-negligible enantioselectivities. In the same year, MacMillan reported on asymmetric Diels–Alder cycloadditions which were efficiently catalyzed by imidazolidinones deriving from natural amino acids. These two seminal reports marked the birth of modern asymmetric organocatalysis. A further important breakthrough in this field happened in 2005, when Jørgensen and Hayashi independently proposed the use of diarylprolinol silyl ethers for the asymmetric functionalization of aldehydes. During the last 20 years, asymmetric organocatalysis has emerged as a very powerful tool for the facile construction of complex molecular architectures. Along the way, a deeper knowledge of organocatalytic reaction mechanisms has been acquired, allowing for the fine-tuning of the structures of privileged catalysts or proposing completely new molecular entities that are able to efficiently catalyze these transformations. This review highlights the most recent advances in the asymmetric synthesis of organocatalysts deriving from or related to proline, starting from 2008.

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Section: Diarylprolinol-related Organocatalystsmentioning

confidence: 99%

Recent Advances in Asymmetric Synthesis of Pyrrolidine-Based Organocatalysts and Their Application: A 15-Year Update

2023

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“…The highly enantioselective Michael reaction of malononitrile and α,β-unsaturated aldehydes catalyzed by a chiral diarylprolinol silyl ether has been developed (Y. Hayashi). 1 The design and synthesis of novel phenylcyclopropane-based secondary amine catalysts and their applications in asymmetric reactions have been summarized in this cluster (T. Kano). 2 A phosphazene base catalyst has been utilized to catalyze the addition reaction of allyl sulfones possessing a diethoxyphosphoryloxy group with α,β-unsaturated ketones (A. Kondoh & M. Terada).…”

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confidence: 99%

Cluster Preface: Development and Applications of Novel Ligands/Catalysts and Mechanistic Studies on Catalysis

Zhang

Zhao

2022

Synlett

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Zhipeng Zhang (left) received his B.S. degree from Shandong University (China) in 2004, and his Ph.D. degree from the Shanghai Institute of Organic Chemistry (SIOC) in 2010 under the supervision of Professor Kuiling Ding. In 2011, he began his postdoctoral studies with Professor Benjamin List at the Max Planck Institute for Coal Research in Mülheim an der Ruhr, Germany. After three years of research on asymmetric organocatalysis, he joined the group of Professor Jin-Quan Yu at The Scripps Research Institute in La Jolla, California as a postdoctoral research associate in 2014. He subsequently worked at the Genomics Institute of the Novartis Research Foundation (GNF) from 2016, before he began his independent career as a professor at the East China University of Science and Technology (ECUST) in 2017. His current research interests include asymmetric catalysis and synthetic methodology, focusing on the design and development of novel chiral ligands and catalysts. Baoguo Zhao (right) received his B.S. degree from Wuhan University in 1996, his M.S. degree from Nanjing University under the supervision of Professor Jianhua Xu in 2002, and his Ph.D. degree from the Shanghai Institute of Organic Chemistry (SIOC) under the supervision of Professor Kuiling Ding in 2006. He subsequently worked with Professor Yian Shi for five years as a postdoctoral fellow at the Department of Chemistry of Colorado State University. In 2011, he joined Shanghai Normal University at the Department of Chemistry as a full professor. His current research interests are in the area of biomimetic asymmetric catalysis, including the development of bioinspired chiral catalysts and synthetic methodologies.

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Asymmetric Michael Reaction of Malononitrile and α,β-Unsaturated Aldehydes Catalyzed by Diarylprolinol Silyl Ether

Cited by 2 publications

References 49 publications

Recent Advances in Asymmetric Synthesis of Pyrrolidine-Based Organocatalysts and Their Application: A 15-Year Update

Recent Advances in Asymmetric Synthesis of Pyrrolidine-Based Organocatalysts and Their Application: A 15-Year Update

Cluster Preface: Development and Applications of Novel Ligands/Catalysts and Mechanistic Studies on Catalysis

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