1020183-41-8Relevant academic research and scientific papers
Diazoacetoacetate enones for the synthesis of diverse natural product-like scaffolds
Shanahan, Charles S.,Truong, Phong,Mason, Savannah M.,Leszczynski, John S.,Doyle, Michael P.
, p. 3642 - 3645 (2013/08/23)
Diazoacetoacetate enones are a new class of Michael acceptors that enable the efficient construction of natural product-like scaffolds. Through their Michael addition reactions, including those with silyl enol ethers, indoles, pyrroles, and amines, δ-functionalized diazoacetoacetates are formed in high yield and with overall operational efficiency. Subsequent catalytic dinitrogen extrusion reactions provide access to a diverse series of natural product-like carbo- and heterocyclic ring systems in only three steps from commercial materials.
Divergent stereocontrol of acid catalyzed intramolecular aldol reactions of 2,3,7-triketoesters: Synthesis of highly functionalized cyclopentanones
Truong, Phong,Shanahan, Charles S.,Doyle, Michael P.
supporting information; experimental part, p. 3608 - 3611 (2012/08/29)
The intramolecular acid catalyzed aldol cyclization of 2,3,7-triketoesters formed from Χ-keto-α-diazo-β-ketoesters provides highly functionalized cyclopentanones with good diastereoselectivity in high overall yields via kinetically controlled and stereodivergent catalytic processes. Lewis acid catalysis gives high selectivity for the 1,2-anti tetrasubstituted cyclopentanones, whereas Bronsted acid catalysis produces the corresponding 1,2-syn diastereomer.
Construction of higly functionalized diazoacetoacentates via catalytic Mukaiyama-Michael reactions
Liu, Yu,Zhang, Yu,Jee, Noel,Doyle, Michael P.
supporting information; experimental part, p. 1605 - 1608 (2009/04/10)
Functionalized diazo acetoacetates are prepared by an efficient Mukaiyama-Michael reaction between methyl 3-(trialkylsilanoxy)-2-diazo-3- butenoate and α,ss-unsaturated enones. Vinyl ether and ketone derivatives are both accessible in good to excellent yi
