Generation and [2,3]-Sigmatropic Rearrangement of Ammonium Ylides from Cyclopropyl Ketones for Chiral Indolizidines with Bridgehead Quaternary Stereocenters.
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DOI: 10.1021/acs.orglett.2c02759
Abstract: A sequence of nucleophilic ring opening of cyclopropyl ketones, N-quaternization, deprotonation, and [2,3]-sigmatropic rearrangement of ammonium ylides has been developed. This method enables efficient synthesis of bicyclic indolizidines bearing bridgehead aza-quaternary stereocenters from easily available… read more here.
Keywords: quaternary stereocenters; rearrangement ammonium; cyclopropyl ketones; ammonium ylides ... See more keywords
Iron-Catalyzed Reductive Ring Opening/gem-Difluoroallylation of Cyclopropyl Ketones.
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DOI: 10.1021/acs.orglett.3c00398
Abstract: By merging C-C and C-F bond cleavage, we developed a regioselective ring opening/gem-difluoroallylation of cyclopropyl ketones with α-trifluoromethylstyrenes, which proceeds under the catalysis of iron with the combination of manganese and TMSCl as the reducing… read more here.
Keywords: gem; gem difluoroallylation; cyclopropyl ketones; opening gem ... See more keywords
Lewis acid catalysed asymmetric cascade reaction of cyclopropyl ketones: concise synthesis of pyrrolobenzothiazoles.
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DOI: 10.1039/d0cc05667g
Abstract: Utilizing the C4 reactive site of cyclopropyl ketones and a chiral N,N'-dioxide-scandium(iii) complex as a catalyst, a concise ring-opening/cyclization/thio-Michael cascade method was developed for the synthesis of chiral benzothiazole derivatives from a simple 2-aminothiophenol material.… read more here.
Keywords: lewis acid; catalysed asymmetric; cyclopropyl; asymmetric cascade ... See more keywords
Some Aspects of Reductive Amination in the Presence of Carbon Monoxide: Cyclopropyl Ketones as Bifunctional Electrophiles
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DOI: 10.1055/s-0036-1588817
Abstract: We conducted detailed studies on CO-assisted reductive chemistry with cyclopropyl ketones as a special type of substrate. Multiple factors influencing the outcome of the reaction have been studied for both ruthenium and rhodium catalysis. An… read more here.
Keywords: bifunctional electrophiles; aspects reductive; reductive amination; reaction ... See more keywords