A new phosphorane obtained from dimethylketene

Bentrude, Wesley G.; Johnson, W. Delmar

doi:10.1021/ja01023a062

Cited by 16 publications

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“…Ketene dimer -lactones have a long and distinguished history of utility in organic synthesis. [1][2][3][4][5][6][7][8] Ketene dimers are among the most interesting -lactones from a synthetic use standpoint due to the presence of an exocyclic double bond with potential for use as a nucleophile following ring-opening reactions. [9][10][11][12][13] Calter and co-workers, and Romo's group have demonstrated that aldoketene homodimer -lactones can be used as building blocks for polypropionate synthesis.…”

Section: Introductionmentioning

confidence: 99%

Addition of heteroatom nucleophiles to ketene dimers

Ibrahim¹,

Harzmann²,

Nalla³

et al. 2021

Arkivoc

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An investigation of the reaction of heteroatom nucleophiles with ketene dimers, with an emphasis on a discussion of diastereoselectivity where applicable, is described. During this study we focused on the reaction of nitrogen-centred nucleophiles (Weinreb amine, lithiated Weinreb amide, and an amino acid derivative), and oxygen-centred nucleophiles (alkoxides). Simple Weinreb amide derivatives of ketene heterodimers were formed in moderate to excellent yield (up to 89%) and excellent retention of chirality (ee up to 91%), albeit with poor diastereoselectivity. The 2-pyridone-catalysed amine ring-opening was also applied to the asymmetric synthesis of a cinnabaramide A intermediate. Finally, the use of amide and alkoxide ring-opening nucleophiles enabled the development of a sequential one-pot reaction with benzaldehyde to afford -lactones in moderate yields (up to 47%) but with good diastereoselectivity (dr up to 24:1).

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