Dirhodium(II) Tetrakis[alkyl 2-oxaazetidine-4(S)-carboxylates]. A New Set of Effective Chiral Catalysts for Asymmetric Intermolecular Cyclopropanation Reactions with Diazoacetates

Doyle, Michael P.; Zhou, Qi; Simonsen, S. H.; Lynch, Vincent M.

doi:10.1055/s-1996-5573

Cited by 79 publications

(54 citation statements)

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“…However, when a tertiary C-H bond is available that could result in a g-lactone product, as is the case with isobutyl phenyldiazoacetate (13), only the g-lactone product is observed (Table 4). Here use of the chiral azetidinone-ligated catalysts gave comparable% ee values for the insertion product (14) to results from Rh 2 (S-DOSP) 4 in pentane.…”

Section: Methodsmentioning

confidence: 99%

Enantioselective β-Lactone Formation from Phenyldiazoacetates via Catalytic Intramolecular Carbon-Hydrogen Insertion

Doyle

May

2001

Synlett

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Section: Methodsmentioning

confidence: 99%

Enantioselective β-Lactone Formation from Phenyldiazoacetates via Catalytic Intramolecular Carbon-Hydrogen Insertion

Doyle

May

2001

Synlett

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“…The most important catalysts are derived from 2-oxopyrrolidines 49 , 2-oxazolidinones 50 , N-acylimidazolidin-2-ones 51 and 2-acetidinones. 52 The nature and structure of the carboxamidate ligands have a large influence on reactivity and selectivity of these complexes. For example, the more strained acetidinones lead to elongation of the Rh -Rh bond and hence increase the reactivity of these complexes.…”

Section: Dirhodium(ii) Carboxamidatesmentioning

confidence: 99%

High symmetry dirhodium(II) paddlewheel complexes as chiral catalysts

Hansen

Davies

2008

Coordination Chemistry Reviews

232

150

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The design and use of chiral dirhodium(II) paddlewheel complexes as catalysts for asymmetric metal carbenoid and metal nitrenoid reactions, and as Lewis acids have become areas of considerable interest during the past two decades. The metal carbenoid chemistry is especially versatile, encompassing transformations such as C-H insertions, cyclopropanations and ylide formation. A number of different classes of dirhodium(II) catalysts have been found to be broadly effective in this chemistry. This review will highlight that many of these catalysts have higher symmetry than the individual chiral ligands themselves. An introduction of theoretical aspects concerning the structure and symmetry of chiral dirhodium(II) complexes will be given followed by an overview of the major classes of catalysts developed to date. Some representative examples of the synthetic potential of these catalysts will also be discussed.

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“…6 Because the amide OCN angle is greater in these compounds than in their five-membered ring counterparts, 7 the Rh-Rh bond length is increased and with it the electronic reactivity of the carboxamidate-ligated catalyst for diazo decomposition. 8 These catalysts have the structure represented by 1, and they differ in reactivity towards diazo esters from their five-membered ring pyrrolidinone (2), 9 oxazolidinone (3), 10 or imidazolidinone (4) …”

Section: Introductionmentioning

confidence: 99%