Chiral bromine–lithium exchange catalyzed by diamines

Perron, Quentin; Praz, Jézabel; Alexakis, Alexandre

doi:10.1016/j.tetasy.2009.02.027

Cited by 22 publications

(8 citation statements)

References 24 publications

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“…Compared to our preliminary communication, [5] we wished to improve first the selectivity and, second, the amount of catalyst, since the use of a catalytic amount of ligand in such reaction remains very challenging. Towards this end, we prepared different new diamines and tried them in our test reaction, where, after the Li-Br exchange, the new dilithiated species is quenched with DMF, to provide dialdehyde 2.…”

Section: Resultsmentioning

confidence: 99%

“…This new methodology appeared to be efficient and we published one of the first desymmetrizations of different classes of prochiral polybrominated compounds by an asymmetric bromine-lithium exchange in the presence of a stoichiometric amount of different diamines with enantiomeric excess up to 63%. [5] At the same time, Kagan et al also reported this new concept, where they presented the desymmetrization of prochiral aromatic or vinylic dihalide substrates in the presence of a stoichiomeric amount of diamines, with enantiomeric excess up to 26%. [6] Then, using Mg instead Li, the group of Brückner described the kinetic resolution of symmetrical alcohols in the presence of stoichiomeric amounts of enantiomerically pure lithium alkoxides.…”

Section: Introductionmentioning

confidence: 99%

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Catalytic Asymmetric Bromine‐Lithium Exchange: A New Tool to Build Axial Chirality

Perron

Alexakis

2010

Adv Synth Catal

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Catalytic Asymmetric Bromine‐Lithium Exchange: A New Tool to Build Axial Chirality

Perron

Alexakis

2010

Adv Synth Catal

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“…Turbo-Grignard chemistry has also been exploited by Nakamura and coworkers [130] to synthesize several aryl-Grignard reagents, which, when treated with Nchloroamines, give an assortment of arylamines (Scheme 5.4). Alexakis [131] has also employed 83 in the preparation of bis(2-bromophenyl)methanol and tert-butyl (bis(2-bromophenyl)methyl)carbamate.…”

Section: Synthetic Applications Of Lithium Magnesiates: Turbo-grignarmentioning

confidence: 99%

Mixed Lithium Complexes: Structure and Applicationin Synthesis

Mulvey

O’Hara

2014

Lithium Compounds in Organic Synthesis

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IntroductionFor half a century, organolithium (C-Li bonded) reagents and lithium amides (N-Li bonded) have played a pivotal role in the development of modern day synthetic chemistry. Reagents in these categories, in particular the butyllithiums (the normal-, secondary-, and tertiary-isomers), lithium diisopropylamide (LDA), lithium 2,2,6,6-tetramethylpiperid-1-ide (LiTMP), and lithium 1,1,1,3,3,3-hexamethyldisilazide (LiHMDS) are utilized in most synthetic laboratories around the world and are especially important in the metallation reaction (that is, the conversion of a relatively inert C-H bond into a more reactive (more chemically pliable) C-Li bond) and in the kinetically operative metal-halogen exchange reactions. The past two decades have witnessed several new classes of constitutionally more complex reagents that contain multimetal and/or multianion formulations that have challenged the dominance of these unimetallic/unianionic reagents in deprotonative/metal-halogen exchange chemistry. This chapter covers some of the rich structural and synthetic chemistry of these new and still emerging systems, detailing only a small selection of what these classes of compounds can offer the chemist at the present time. Structural Chemistry of Heterometallic Lithium ComplexesStructure is inextricably and mutually linked to reactivity; hence, much recent research activity has focused on the elucidation of solid-state and solution structures of lithium organometallics and amides. This section concentrates on the structural chemistry of lithium-containing mixed-metal complexes, focusing particularly on mixed s-block (Group 1/Group 1 or Group 1/Group 2) complexes, and those containing the Group 12 d 10 metal zinc, which is commonly regarded as a displaced alkaline earth metal. In recent years, heterometallic sodium reagents (particularly sodium zincates, magnesiates, aluminates, etc.) have received a great Lithium Compounds in Organic Synthesis: From Fundamentals to Applications, First Edition. Edited by Renzo Luisi and Vito Capriati.

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“…Das Problem bestand in der mehrfachen Lithiierung von 4. [15] Wir zeigten kürzlich, dass die Phosphanylierung von Arylradikalen eine hocheffiziente Methode zur Synthese von Arylphosphanen ist. [16] Einkristalle von trans-2 und cis-2 wurden aus einer Lçsung von CH 2 Cl 2 /n-Hexan gewonnen und durch Rçnt-gendiffraktometrie analysiert (Abbildung 2).…”

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Bis(phosphoryl)‐verbrückte Biphenyle durch radikalische Phosphanylierung: Synthese, photophysikalische und elektrochemische Eigenschaften

et al. 2011

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Die effiziente vierfache radikalische Phosphanylierung von 2,2,2′,2′‐Tetrabrombiphenyl mit einem Bis(stannyl)phosphan, gefolgt von P‐Oxidation, führt zu gespannten Biphenylen mit zwei Phosphorylbrücken (siehe Bild). Verlängerte π‐konjugierte Verbindungen mit diesem Biphenylkern können auch durch die mehrfache radikalische Phosphanylierung synthetisiert werden. Die zwei Phosphorylbrücken machen das Biphenyl zu einem einzigartigen elektronenziehenden Gerüst.

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Chiral bromine–lithium exchange catalyzed by diamines

Cited by 22 publications

References 24 publications

Catalytic Asymmetric Bromine‐Lithium Exchange: A New Tool to Build Axial Chirality

Catalytic Asymmetric Bromine‐Lithium Exchange: A New Tool to Build Axial Chirality

Mixed Lithium Complexes: Structure and Applicationin Synthesis

Bis(phosphoryl)‐verbrückte Biphenyle durch radikalische Phosphanylierung: Synthese, photophysikalische und elektrochemische Eigenschaften

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