The Journal of Organic Chemistry

Branched-chain carbohydrate lactones from a samarium (II) iodide-promoted serial deoxygenation-carbonyl addition reaction

EJ Enholm, S Jiang, K Abboud

Index: Enholm, Eric J.; Jiang, Shujun; Abboud, Khalil Journal of Organic Chemistry, 1993 , vol. 58, # 15 p. 4061 - 4069

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Citation Number: 23

Abstract

A new deoxygenation-carbonyl addition reaction mediated by samarium (I1) iodide (SmI2) in THFI HMPA was examined with carbohydrate lactones and several substrates containing an a-alkoxy carboxylic ester. In a single reaction, these compounds were deoxygenated and subsequently coupled to several ketones by a carbonyl addition reaction. The first reactions studied simple ester and ketone adducts which were later elaborated to more complex ...