- Dimethylamine adducts of allylic triorganoboranes as effective reagents for Petasis-type homoallylation of primary amines with formaldehyde
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Dimethylamine adducts of triallyl-, triprenyl- and trans-cinnamyl(dipropyl)borane are effective reagents for mild homoallylation of primary amines with aqueous formaldehyde in MeOH without an inert atmosphere. A new concept is proposed for the explanation of the high stability of allylborane-amine adducts in aqueous MeOH.
- Kuznetsov, Nikolai Yu.,Tikhov, Rabdan M.,Strelkova, Tatiana V.,Bubnov, Yuri N.
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supporting information
p. 7115 - 7119
(2018/10/23)
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- New enolate-carbodiimide rearrangement in the concise synthesis of 6-amino-2,3-dihydro-4-pyridinones from homoallylamines
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Three-step synthesis of 6-amino-2,3-dihydro-4-pyridinones from homoallylamines involving NBS-mediated cyclization of N-(3-butenyl)ureas to 6-(bromomethyl)-2-iminourethanes, dehydrohalogenation and a novel rearrangement as a key step has been developed. Th
- Kuznetsov,Tikhov,Godovikov,Khrustalev,Bubnov
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supporting information
p. 4283 - 4298
(2016/05/24)
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- Chiral 1,2-dialkenyl diaziridines: Synthesis, enantioselective separation, and nitrogen inversion barriers
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Trans-1,2-Disubstituted diaziridines form stable enantiomers at ambient conditions because of the two stereogenic pyramidal nitrogen atoms. Functionalized trans-1,2-disubstituted diaziridines can be utilized as a chiral switching moiety between two enantiomeric states in more complex molecular structures. However, the synthesis of functionalized diaziridines is quite challenging, because of the limited tolerance of reaction conditions that can be applied. Here we present a strategy to make trans-1,2-disubstituted diaziridines accessible as versatile building blocks in C-C-bond formations, i.e., the Heck reaction, and therefore introducing aryl substituents. The synthesis of trans-1,2-dialkenyl diaziridines with terminal alkenyl substituents and their stereodynamic properties are described.
- Zawatzky, Kerstin,Kamuf, Matthias,Trapp, Oliver
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p. 156 - 162
(2015/03/04)
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- Synthesis of Azabicycles via Cascade Aza-Prins Reactions: Accessing the Indolizidine and Quinolizidine Cores
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The first detailed studies of intramolecular aza-Prins and aza-silyl-Prins reactions, starting from acyclic materials, are reported. The methods allow rapid and flexible access toward an array of [6,5] and [6,6] aza-bicycles, which form the core skeletons of various alkaloids. On the basis of our findings on the aza-Prins and aza-silyl-Prins cyclizations, herein we present simple protocols for the intramolecular preparation of the azabicyclic cores of the indolizidines and quinolizidines using a one-pot cascade process of N-acyliminium ion formation followed by aza-Prins cyclization and either elimination or carbocation trapping. It is possible to introduce a range of different substituents into the heterocycles through a judicial choice of Lewis acid and solvent(s), with halo-, phenyl-, and amido-substituted azabicyclic products all being accessed through these highly diastereoselective processes.
- Chio, Freda K. I.,Guesné, Sébastien J. J.,Hassall, Lorraine,McGuire, Thomas,Dobbs, Adrian P.
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p. 9868 - 9880
(2015/11/03)
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- Synthesis of 3-oxoazacyclohept-4-enes by ring-closing metathesis. Application to the synthesis of an inhibitor of cathepsin K
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The ring-closing metathesis allows the formation of 3-oxoazacyclohept-4-enes from but-3-enamine. By using this methodology, the synthesis of an inhibitor of cathepsin K was achieved in 10 steps from but-3-enamine.
- Taillier, Catherine,Hameury, Thomas,Bellosta, Veronique,Cossy, Janine
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p. 549 - 554
(2007/10/03)
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- Self-selection in olefin cross-metathesis: The effect of remote functionality
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(Chemical Equation Presented) Olefin cross-metathesis (CM) is potentially an attractive method for generating dynamic combinatorial libraries (DCLs). In order for the CM reaction to be useful for DCL production, the course of the reaction and product dist
- McNaughton, Brian R.,Bucholtz, Kevin M.,Camaano-Moure, Ana,Miller, Benjamin L.
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p. 733 - 736
(2007/10/03)
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- Synthesis of azetidine, pyrrolidines and piperidine by intramolecular cyclization of ω-Azidoboranes.
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This paper describes the development of efficient routes to azetidine, pyrrolidines and piperidines by creation of a carbon-nitrogen bond.Two complementary syntheses of these heterocycles were studied : the cyclization of ω-azidoboronic esters by treatment with boron trichloride, and the one pot hydroboration of an ω-azidoalkene and intramolecular reductive alkylation.The scope and limitations of these two promising approaches are reported.Keywords: azides / boronic esters / boranes / intermolecular cyclization / azetidine / pyrrolidine / piperidine / pyrrolizidine
- Jego, J. M.,Carboni, B.,Vaultier, M.
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p. 554 - 565
(2007/10/02)
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