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Metal-catalyzed Carbenoid Reactions with Iodonium and Sulfonium Ylides by Paul Müller; Daniel Fernandez; Patrice Nury; Jean-Claude Rossier is a Chemistry article available to read on EtoBox.

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Transition metal-catalyzed decomposition of phenyliodonium and diphenylsulfonium ylides was investigated with regard to application in asymmetric carbenoid reactions. Phenyliodonium ylides react in the presence of Rh(II) catalysts with the same selectivity in inter-and intramolecular cyclopropanations as the corresponding diazo compounds, and intramolecular CH insertions proceed with identical enantioselectivities. With diphenylsulfonium ethoxycarbonylmethylide the Cu(I)-catalyzed cyclopropanation of olefins affords trans/cis ratios and asymmetric inductions identical with those of diazo compounds, but with Rh(II) catalysts some small, although significant, selectivity variations occur, which are ascribed to coordination of diphenyl sulfide to one of the coordination sites of the catalyst.

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Author

Paul Müller; Daniel Fernandez; Patrice Nury; Jean-Claude Rossier

Publisher

John Wiley and Sons; Wiley (John Wiley & Sons); John Wiley & Sons Inc.; Wiley (ISSN 0894-3230)

Published

1998

Language

EN

Field

Chemistry (Physical Sciences)