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Chiral Lewis acid

About: Chiral Lewis acid is a research topic. Over the lifetime, 625 publications have been published within this topic receiving 20403 citations.


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TL;DR: Shū Kobayashi was born in 1959 in Tokyo, Japan and studied chemistry at the University of Tokyo and received his Ph.D. in 1988 (Professor T. Mukaiyama), and received the first Springer Award in Organometallic Chemistry in 1997.
Abstract: Chiral nitrogen-containing compounds are widely distributed in nature and include many biologically important molecules (Chart 1). In these compounds, the nitrogen-containing units are known to play important roles for their bioactivities. For the synthesis of these chiral nitrogen-containing building blocks, use of imines as electrophiles is the most promising and convenient route.1 While many approaches using chiral imines or chiral nucleophiles have been reported,1 these diastereoselective reactions have some disadvantages. First, the procedures to introduce chiral auxiliaries to substrates and to remove them after the diastereoselective reactions are often tedious. Second, more than stoichiometric amounts of chiral sources are needed to obtain chiral compounds according to these reactions. On the other hand, catalytic enantioselective reactions provide the most efficient methods for the synthesis of chiral compounds,2 because large quantities of chiral compounds are expected to be prepared using small amounts of chiral sources. While much progress has been made recently in catalytic enantioselective reactions of aldehydes and ketones such as aldol,3 allylation,4 Diels-Alder,5 cyanation reactions,6 reduction,1b,2b etc., progress in catalytic enantioselective reactions of imines is rather slow. There are some difficulties in performing catalytic enantioselective reactions of imines. For example, in the cases of chiral Lewis acid promoted asymmetric Shū Kobayashi was born in 1959 in Tokyo, Japan. He studied chemistry at the University of Tokyo and received his Ph.D. in 1988 (Professor T. Mukaiyama). After spending 11 years at Science University of Tokyo (SUT), he moved to Graduate School of Pharmaceutical Sciences, University of Tokyo, in 1998. His research interests include development of new synthetic methods, development of novel catalysts (especially chiral catalysts), organic synthesis in water, solid-phase organic synthesis, total synthesis of biologically interesting compounds, and organometallic chemistry. He received the first Springer Award in Organometallic Chemistry in 1997.

1,356 citations

Journal ArticleDOI
TL;DR: "planar-chiral" derivatives of 4-(dimethylamino)pyridine (DMAP) are developed, a highly versatile nucleophilic catalyst that are effective in a diverse array of processes, including the Staudinger synthesis of beta-lactams, the acylation of silyl ketene acetals, and the kinetic resolution of amines.
Abstract: Whereas chiral Lewis acid catalysis has been intensively investigated, chiral Lewis base (nucleophilic) catalysis has been comparatively neglected. We have developed “planar-chiral” derivatives of 4-(dimethylamino)pyridine (DMAP), a highly versatile nucleophilic catalyst, that are effective in a diverse array of processes, including the Staudinger synthesis of β-lactams, the acylation of silyl ketene acetals, and the kinetic resolution of amines.

375 citations

Journal ArticleDOI
TL;DR: The first general approach to enantioselective catalysis of the Diels−Alder reaction with simple ketone dienophiles has been accomplished with the use of iminium catalysis and a new chiral amine catalyst has been developed that allows a variety of monodentate cyclic and acyclic ketones to successfully participate in enantiosedive [4 + 2] cycloadditions.
Abstract: The first general approach to enantioselective catalysis of the Diels−Alder reaction with simple ketone dienophiles has been accomplished. The use of iminium catalysis has enabled enantioselective access to a fundamental Diels−Alder reaction variant that has previously been unavailable using chiral Lewis acid catalysis. A new chiral amine catalyst has been developed that allows a variety of monodentate cyclic and acyclic ketones to successfully participate in enantioselective [4 + 2] cycloadditions. A wide spectrum of cyclic and acyclic diene substrates can also be accommodated in this new organocatalytic transformation. A computational model is provided that is in accord with the sense of enantioinduction observed for all reactions conducted during the course of this study.

368 citations

Journal ArticleDOI
Jacob M. Janey1
TL;DR: A synopsis of this ever-growing field of catalytic, enantioselective Lewis acid and Lewis base catalysis is provided and some of the challenges that still remain are highlighted.
Abstract: The direct introduction of either a nitrogen or oxygen atom adjacent to a carbonyl group in a catalytic, enantioselective manner using both chiral Lewis acid and Lewis base catalysis has been described recently. The enantiomerically enriched products of these reactions, such as α-amino acids, represent fundamental building blocks for the construction of complex natural products and other important bioactive molecules. This Minireview provides a synopsis of this ever-growing field and highlights some of the challenges that still remain.

290 citations

Journal ArticleDOI
TL;DR: A new approach that takes advantage of N-heterocyclic carbene/Lewis acid cooperative catalysis provides access to cis-1,3,4-trisubstituted cyclopentenes from enals and chalcone derivatives with high levels of diastereoselectivities and enantioselectivity.
Abstract: A new approach that takes advantage of N-heterocyclic carbene/Lewis acid cooperative catalysis provides access to cis-1,3,4-trisubstituted cyclopentenes from enals and chalcone derivatives with high levels of diastereoselectivity and enantioselectivity. The presence of Ti(OiPr)4 as the Lewis acid allows for efficient substrate preorganization, which translates into high levels of diastereoselectivity. Additionally, we demonstrate the possibility of controlling the absolute stereochemistry of NHC-catalyzed reactions by employing a catalytic amount of a chiral Lewis acid as the unique source of optically active promoter.

272 citations


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Performance
Metrics
No. of papers in the topic in previous years
YearPapers
20231
20229
20219
20204
201914
20188