Enantioselective Photochemical Reactions of 2-Pyridones in Solution

Bach, Thorsten; Bergmann, Hermann; Harms, Klaus

doi:10.1021/ol007004t

Cited by 66 publications

(34 citation statements)

References 18 publications

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“…The formation of H-B pyridone dimers was first used by Beak and Ziegler to enhance the photodimerization of distant cinnamates in solution. [16] More recently, similar interactions formed the basis of the enantioselective dimerization of pyrimidones [17] ( Figure 4) and their cycloaddition to aromatic aldehydes and ketones. [18] By exerting enantiotopic control over photochemical reactions, their usefulness in organic synthesis can be expanded significantly.…”

Section: Supramolecular Photochemistry In Solutionmentioning

confidence: 94%

Exciting Supramolecular Architectures: Light‐Induced Processes and Synthetic Transformations in Noncovalent Assemblies

Huang

Bassani

2005

Eur J Org Chem

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Keywords: Supramolecular chemistry / Photochemistry / Self-assembly / ReceptorsThis review outlines recent advances in the area of supramolecular photochemistry, particularly with respect to the use of noncovalent interactions to direct and control excited-state processes in the solid phase and in solution.Light is a versatile tool in modern science. The growing momentum of nanotechnology has rekindled interest in photochemical processes, which play an important role in numerous applications in which light is used as a source of energy or to transmit information to and from molecular components. The latter are frequently arranged in a con- [a] (Physical Chemistry Division, 2004) and the Grammaticakis-Neuman Prize of the Swiss Chemical Society (2005).MICROREVIEWS: This feature introduces the readers to the authors' research through a concise overview of the selected topic. Reference to important work from others in the field is included. strained environment, which imparts new − though at times unexpected − behavior. This microreview is focused on the recent work in this growing area, which, interestingly, is not necessarily the dominion of photochemists. It is immediately obvious that design and synthesis play a leading role in the development of some of the more interesting systems reported. Photoinduced processes frequently encountered include fluorescence, E Ǟ Z isomerization of conjugated double bonds, energy and electron transfer, and cyclodimerization reactions. Their behavior, and at times their outcome, can be influenced by the presence of noncovalent interactions that impart structural order or rigidity to the

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Section: Supramolecular Photochemistry In Solutionmentioning

confidence: 94%

Exciting Supramolecular Architectures: Light‐Induced Processes and Synthetic Transformations in Noncovalent Assemblies

Huang

Bassani

2005

Eur J Org Chem

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“…In the presence of chiral template 44a , 61 and 62 are produced in remarkable ee ' s of 84 -87%. 115 Compound 63 (Scheme 4.24 ), which was originally developed as a gastroprokinetic agent, and its epimer 64 were incidentally found to strongly bind affords HT dimer 5b in − 36% ee and HH dimer 5c in − 40% ee in CH 2 Cl 2 at − 50 ° C. In contrast, epimer 64 , which forms an open rather than stacked complex with AC, affords the same cyclodimers but only in poor enantioselectivity of < 3% ee.…”

Section: Intermolecular Photoreactions Mediated By Chiral Templatesmentioning

confidence: 99%

Supramolecular Photochirogenesis

Yang¹,

Inoue²

2011

Supramolecular Photochemistry

132

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“…Introducing chiral molecules in the reaction mixture able to give complexes with a reduced mobility. Some applications have been reported recently in cycloaddition reactions [53][54][55][56][57], in Norrish II reactions [31], in photocyclization [32], and in photoenolizations and Diels-Alder (Scheme 13) [58][59][60][61]. 3.…”

Section: Molecules With Prevented Mobilitymentioning

confidence: 99%

Concepts of Stereoselective Photochemistry and a Case Study: the Paterno-Buchi Reaction

D’Auria¹,

Racioppi

2009

COC

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The main methods reported in literature to obtain stereoselective photochemical reaction is reviewed. The most important approached attempted to obtain stereoselective photochemical reaction are:1.) the use of diastereoselective photochemical reactions, 2.) the use of molecules with prevented mobility (this approach can be obtained 1. introducing chiral auxiliary, 2. introducing chiral molecules in the reaction mixture able to give complexes with a reduced mobility, 3. performing the reaction in organized media such as zeolites or cyclodextrins, 4. performing the reaction on single crystal, 5. performing the reaction on single crystals of molecules able to give crystal in chiral space group, and, 6. finally performing the reaction in solid phase on inclusion complexes of the substrate with chiral molecules); 3.) using chiral solvents and chiral light, and 4.) using chiral photosensitizers.The case of the diastereoselective Paternò-Büchi reaction on furan derivatives is also discussed.

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Enantioselective Photochemical Reactions of 2-Pyridones in Solution

Cited by 66 publications

References 18 publications

Exciting Supramolecular Architectures: Light‐Induced Processes and Synthetic Transformations in Noncovalent Assemblies

Exciting Supramolecular Architectures: Light‐Induced Processes and Synthetic Transformations in Noncovalent Assemblies

Supramolecular Photochirogenesis

Concepts of Stereoselective Photochemistry and a Case Study: the Paterno-Buchi Reaction

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