124097-05-8Relevant articles and documents
General Cyclopropane Assembly by Enantioselective Transfer of a Redox-Active Carbene to Aliphatic Olefins
Montesinos-Magraner, Marc,Costantini, Matteo,Ramírez-Contreras, Rodrigo,Muratore, Michael E.,Johansson, Magnus J.,Mendoza, Abraham
supporting information, p. 5930 - 5935 (2019/02/24)
Asymmetric cyclopropane synthesis currently requires bespoke strategies, methods, substrates, and reagents, even when targeting similar compounds. This approach slows down discovery and limits available chemical space. Introduced herein is a practical and versatile diazocompound and its performance in the first unified asymmetric synthesis of functionalized cyclopropanes. The redox-active leaving group in this reagent enhances the reactivity and selectivity of geminal carbene transfer. This effect allowed the asymmetric cyclopropanation of various olefins, including unfunctionalized aliphatic alkenes, that enables the three-step total synthesis of (?)-dictyopterene A. This unified synthetic approach delivers high enantioselectivities that are independent of the stereoelectronic properties of the functional groups transferred. Our results demonstrate that orthogonally differentiated diazocompounds are viable and advantageous equivalents of single-carbon chirons.
Hydroalkylation of Olefins to Form Quaternary Carbons
Green, Samantha A.,Huffman, Tucker R.,McCourt, Ruairí O.,Van Der Puyl, Vincent,Shenvi, Ryan A.
supporting information, p. 7709 - 7714 (2019/05/22)
Metal-hydride hydrogen atom transfer (MHAT) functionalizes alkenes with predictable branched (Markovnikov) selectivity. The breadth of these transformations has been confined to π-radical traps; no sp3 electrophiles have been reported. Here we describe a Mn/Ni dual catalytic system that hydroalkylates unactivated olefins with unactivated alkyl halides, yielding aliphatic quaternary carbons.
A new method of synthesis of 6-substituted piperidine-2,4-diones from homoallylamines
Kuznetsov, Nikolai Yu.,Maleev, Victor I.,Khrustalev, Victor N.,Mkrtchyan, Anna F.,Godovikov, Ivan A.,Strelkova, Tatyana V.,Bubnov, Yuri N.
, p. 334 - 344 (2012/02/16)
Mono- and dihomoallylamines serve as convenient precursors for the preparation of 6-substituted piperidine-2,4-diones. This transformation is based, on the one hand, on a simple and well-known halocyclocarbamation reaction proceeding by the addition of a