Chiral Silver Amide-Catalyzed Enantioselective [3 + 2] Cycloaddition of α-Aminophosphonates with Olefins

Yamashita, Yasuhiro; Guo, Xun‐Xiang; Takashita, Ryuta; Kobayashi, Shū

doi:10.1021/ja100101n

Cited by 96 publications

(24 citation statements)

References 39 publications

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“…77 The first catalytic asymmetric 1,3-dipolar cycloadditions of Schiff bases of α-aminophosphonates 133 with olefins have been described by Kobayashi and coworkers (Scheme 64). 78 The reaction is catalyzed by chiral silver amide complexes bearing (R)-DTBM-SEGPHOS 113, and proline phosphonic analogs 134 were obtained in high yield with excellent diastereo-and enantioselectivities.…”

Section: Catalytic Asymmetric 13-dipolar Cycloadditions From Other Amentioning

confidence: 99%

4.22 Intermolecular 1,3-Dipolar Cycloadditions of Alkenes, Alkynes, and Allenes

Wang

Tang

2014

Comprehensive Organic Synthesis II

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Section: Catalytic Asymmetric 13-dipolar Cycloadditions From Other Amentioning

confidence: 99%

4.22 Intermolecular 1,3-Dipolar Cycloadditions of Alkenes, Alkynes, and Allenes

Wang

Tang

2014

Comprehensive Organic Synthesis II

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“…13 However, it was just in 2002 when the first substoichiometric catalytic (3 14 mol%) enantioselective transformation was successfully reported by Zhang 15 and coworkers using a chiral diphosphane/silver(I) complex [21]. involving α-iminoesters, the generation of stabilized metallo-1,3-dipoles 13 has been achieved starting from α-iminophosphonates using chiral silver(I) 14 complexes [27] and α-iminonitriles employing chiral copper(I) complexes 15 [28]. (5 17 mol-%) was used instead the er was also lower than the result described for 18 the 1:1 mixture.…”

Section: Enantioselective Methodsmentioning

confidence: 99%

Enantioselective synthesis of proline derivatives by 1,3-dipolar cycloadditions

Nájera

Sansano

2011

Monatsh Chem

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“…Notable examples include the use of Cu/PyBIDINE (Cu/L30) [60] and Ag/L20 [61] systems, which catalyze the cycloaddition of imino esters to nitroalkenes and electron-deficient alkenes, respectively (Scheme 9.6). In contrast, the 1,3-DC between α-aminophosphonate Schiff bases 58 and alkenes 59, catalyzed by Ag/DTBM-SEGPHOS (Ag/L31) catalyst, yields the exo product 60 as the major diastereomer in 99% ee with >99 : 1 selectivity [62]. In contrast, the 1,3-DC between α-aminophosphonate Schiff bases 58 and alkenes 59, catalyzed by Ag/DTBM-SEGPHOS (Ag/L31) catalyst, yields the exo product 60 as the major diastereomer in 99% ee with >99 : 1 selectivity [62].…”

Section: Other Addition Reactionmentioning

confidence: 99%

An Overview of Recent Developments in Metal‐Catalyzed Asymmetric Transformations

Sandoval¹,

Noyori²,

Zhou³

et al. 2012

Organic Chemistry – Breakthroughs and Perspectives

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IntroductionCatalysis is the most efficient means to bring about a chemical transformation, since the catalyst used is in principle not consumed in the process and can continuously catalyze a given process to generate a product. When a metal catalyst is employed, the catalysis itself generally stems from the inherent properties of the given metal(s) -Lewis acidity, variable oxidation states, coordination sphere properties, and so on. For metal-based molecular catalysis, however, the ligand frameworks about the metal center can have a dramatic effect on the stability and catalytic performance, and/or actively participate through metal-ligand cooperative processes. The use of chiral ligands generates a chiral 3D environment that effectively controls the stereo-outcome of the chemical transformation, thus giving rise to asymmetric catalysis. Such strategies have been instrumental in the development of modern synthetic strategies at the academic and industrial levels, and constitute a cornerstone for modern organic syntheses.This chapter aims to give a general overview of the types of metal-catalyzed processes currently possible, with emphasis on the catalytic transformation itself. Only representative examples from the last decade are given to highlight the catalytic process without aiming to be comprehensive [1]. More emphasis is given to C-C bond-forming metal-catalyzed asymmetric syntheses due to the rapid developments in this area in recent years. Mostly intermolecular processes are given as examples and typically the results presented are under optimum conditions and represent the highest efficiency and selectivity obtained. It should be mentioned that a similar chapter using different authors and examples may have been used to illustrate advances in a given area, which is a tribute to the excellence and scope of contemporary research advancing asymmetric catalysis.Contributions where the metal is involved as a (chiral) reagent or systems where enantioselection stems from substrate control or use of chiral auxiliaries were not considered. Catalytically active supramolecular assemblies where metals act as linkers or transformations involving metal-containing enzymes were judged inappropriate. Similarly, selective metal-catalyzed polymerization processes and concurrent breakthroughs in organocatalysis are not included.

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Chiral Silver Amide-Catalyzed Enantioselective [3 + 2] Cycloaddition of α-Aminophosphonates with Olefins

Cited by 96 publications

References 39 publications

4.22 Intermolecular 1,3-Dipolar Cycloadditions of Alkenes, Alkynes, and Allenes

4.22 Intermolecular 1,3-Dipolar Cycloadditions of Alkenes, Alkynes, and Allenes

Enantioselective synthesis of proline derivatives by 1,3-dipolar cycloadditions

An Overview of Recent Developments in Metal‐Catalyzed Asymmetric Transformations

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