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Regio- and stereoselectivity in the addition reactions of CH-acids to aldehydes under the conditions of phase-transfer catalysis

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Abstract

The regio- and stereoselectivity of the reactions of carbanions, generated from alkanals, carboxylates of the type XYCHCOOEt (X = EtOOC, CN, Ac; Y = H, Br), or derivatives of 3-methyl-4-phosphono-2-butenoic acid using PTC techniques, with aldehydes of various types (alkanals, α,β-enals, cross-conjugated enedials, benzaldehydes,etc.) are reviewed. The factors affecting the outcome of these reactions are discussed. The carbanion analogs, triphenylphosphorus ylides, are shown to attack selectively at one of the aldehyde groups of aromatic dialdehydes. The regularities found for the title reactions were used in the syntheses of some biologically active isoprenoids.

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  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation

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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1867–1885, October, 1995.

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Kryshtal, G.V., Serebryakov, E.P. Regio- and stereoselectivity in the addition reactions of CH-acids to aldehydes under the conditions of phase-transfer catalysis. Russ Chem Bull 44, 1785–1804 (1995). https://doi.org/10.1007/BF00707200

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