Pd??Catalyzed Nucleophilic Alkylation of Aliphatic Aldehydes with Allyl Alcohols: Allyl, 2??Tetrahydrofuryl, and 2??Tetrahydropyranyl Ethers as Useful C3, C4, and C5 …

M Kimura, M Shimizu, K Shibata…

Index: Kimura, Masanari; Shimizu, Masamichi; Shibata, Kazufumi; Tazoe, Minoru; Tamaru, Yoshinao Angewandte Chemie - International Edition, 2003 , vol. 42, # 29 p. 3392 - 3395

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Citation Number: 70

Abstract

diastereoselectivity found for the reactions carried out with cinnamyl alcohol is modest and seems to depend on the steric bulk of the alkyl chain of the aldehydes and ranges from syn: anti= 1: 18 (cyclo-C6H11CHO) to 1: 2 (nC 5H11CHO). It is worth noting that, despite insitu formation of zinc alkoxides, no aldol-, Cannizzaro-, or Tischchenko-type products were detected at all in these reactions. We envisaged that the reaction conditions that were ...

~89%

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