Synthesis of <i>trans</i>-2-Substituted Cyclopropylamines from α-Chloroaldehydes

West, Michael S.; Mills, L. Reginald; McDonald, Tyler; Lee, Jessica B.; Ensan, Deeba; Rousseaux, Sophie

doi:10.1021/acs.orglett.9b03172

Cited by 12 publications

(5 citation statements)

References 56 publications

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“…Flash column chromatography was carried out using 200–300 mesh silica gel. All of the α-chloro hydrazones , and α-chloro aliphatic aldehydes , used in this work were synthesized according to known protocols.…”

Section: Experimental Sectionmentioning

confidence: 99%

N-Heterocyclic Carbene-Promoted [4+2] Annulation of α-Chloro Hydrazones with α-Chloro Aliphatic Aldehydes to Access Enantioenriched Dihydropyridazinones

Zhou

2022

J. Org. Chem.

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An expeditious protocol for the assembly of chiral 4,5-dihydropyridazin-3(2H)-ones from α-chloro hydrazones and α-chloro aliphatic aldehydes via N-heterocyclic carbene (NHC) catalysis is outlined. These in situ-generated 1,2-diaza-1,3-dienes undergo asymmetric [4+2] annulation with NHC-bound enolates to afford the desired products bearing a stereogenic center at the C4 position. The notable features of this approach include good to excellent enantioselectivities, high functional group tolerance, mild reaction conditions, simple operating procedures, and compatibility with gram-scale synthesis.

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Section: Experimental Sectionmentioning

confidence: 99%

N-Heterocyclic Carbene-Promoted [4+2] Annulation of α-Chloro Hydrazones with α-Chloro Aliphatic Aldehydes to Access Enantioenriched Dihydropyridazinones

Zhou

2022

J. Org. Chem.

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“…In 2019, our group reported a new strategy for the formation of cyclopropylamines (257), which uses α-chloroaldehydes (255) as the starting materials (Scheme 59). 139 In this protocol, treatment of 255 with bis(iodozincio)methane generates the Zn homoenolate intermediate (256). As an electrophilic Zn homoenolate, this intermediate can be trapped in the same pot with an amine to form the cyclopropylamine (257).…”

Section: Trapping Of the Homoenolate Carbonyl With Nucleophilesmentioning

confidence: 99%

Selective Carbon–Carbon Bond Cleavage of Cyclopropanols

et al. 2020

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The carbon–carbon (C–C) bond cleavage of cyclopropanols is a wide area of research with much current activity. This review highlights new developments in this area over the past two decades. A summary is made of the three main reactivity modes, namely, homoenolate chemistry, β-keto radical chemistry, and acid-catalyzed ring-opening, as well as all other methods for the C–C bond cleavage and functionalization of cyclopropanols, including base-mediated ring-opening, metal-catalyzed C–C insertions and eliminations, oxidative fragmentation using hypervalent iodine reagents, reactions of donor–acceptor cyclopropanols, and pericylic reactions. Emphasis is placed on the synthetic utility of cyclopropanols and related derivatives, which have emerged as unique three-carbon synthons.

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“…5 Interestingly, cyclopropylamines could be nicely prepared via trapping a zinc homoenolate intermediate with an amine. 6 In addition to the above-mentioned methods, cyclopropanation of alkenes with carbenoids is a straightforward route to diversely functionalized cyclopropylamines. 7 Surprisingly, the methylene transfer reaction of N -vinylimides is still rare.…”

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confidence: 99%