165336-55-0Relevant academic research and scientific papers
Tandem chain extension-iodomethylation reactions: formation of α-functionalized γ-keto carbonyls
Pu, Qinglin,Wilson, Emerald,Zercher, Charles K.
, p. 8045 - 8051 (2008)
Sequential exposure of a zinc-organometallic intermediate, generated through a zinc carbenoid-mediated chain extension reaction of a β-keto carbonyl, to trimethylsilylchloride and iodine provided regioselective formation of an α-iodomethyl-γ-keto carbonyl. The iodomethyl functionality can be further manipulated to provide side chains that are potential mimics of α-amino acid side chains.
Formation of γ-lactones through CAN-mediated oxidative cleavage of hemiketals
Jacobine, Alexander M.,Lin, Weimin,Walls, Bethany,Zercher, Charles K.
supporting information; experimental part, p. 7409 - 7412 (2009/05/07)
(Chemical Equation Presented) The generation of substituted γ-lactones can be accomplished through application of a tandem chain extension-aldol reaction, followed by CAN-mediated oxidative cleavage of the aldol product. The oxidative cleavage requires the intermediacy of a hemiketal and the presence of an α-heteroatom. Formation of the γ-lactone through the oxidative cleavage is used to assign stereochemistry of the aldol reaction and as the final step in a short synthesis of members of the phaseolinic acid family of natural products.
