Copper diisobutyl-t-butoxyaluminum hydride: A novel reagent for chemoselective reduction of tertiary amides over esters
Sign Up to like & getrecommendations! Published in 2018 at "Tetrahedron Letters"
DOI: 10.1016/j.tetlet.2018.04.082
Abstract: Abstract We demonstrate that copper diisobutyl-t-butoxyaluminum hydride, readily prepared from lithium diisobutyl-t-butoxyaluminum hydride and CuI, effectively and chemoselectively reduces tertiary amides over esters at ambient temperature, affording the corresponding aldehydes in excellent yields. read more here.
Keywords: butoxyaluminum hydride; copper diisobutyl; diisobutyl butoxyaluminum; tertiary amides ... See more keywords
Fully Automated Flow Protocol for C(sp3)-C(sp3) Bond Formation from Tertiary Amides and Alkyl Halides.
Sign Up to like & getrecommendations! Published in 2023 at "Organic letters"
DOI: 10.1021/acs.orglett.3c01390
Abstract: Herein, we present a novel C(sp3)-C(sp3) bond-forming protocol via the reductive coupling of abundant tertiary amides with organozinc reagents prepared in situ from their corresponding alkyl halides. Using a multistep fully automated flow protocol, this… read more here.
Keywords: fully automated; sp3 bond; alkyl halides; sp3 sp3 ... See more keywords
Catalyst-Free Transamidation of Aromatic Amines with Formamide Derivatives and Tertiary Amides with Aliphatic Amines.
Sign Up to like & getrecommendations! Published in 2019 at "Organic letters"
DOI: 10.1021/acs.orglett.8b03542
Abstract: A simple catalyst- and promoter-free protocol has been developed for the transamidation of weakly nucleophilic aromatic amines with formamide derivatives and low-reactivity tertiary amides with aliphatic amines. This strategy is advantageous because no catalyst or… read more here.
Keywords: amines formamide; aliphatic amines; aromatic amines; formamide derivatives ... See more keywords
Catalytic Reductive Functionalization of Tertiary Amides using Vaska’s Complex: Synthesis of Complex Tertiary Amine Building Blocks and Natural Products
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DOI: 10.1021/acscatal.0c02377
Abstract: The tertiary amide is a ubiquitous functional group and plays an irreplaceable role in medicinal chemistry. Its robust nature has meant—in the past—that selective manipulation of this motif remaine... read more here.
Keywords: using vaska; reductive functionalization; amides using; functionalization tertiary ... See more keywords
Iridium-catalyzed Reductive Nucleophilic Addition to Tertiary Amides
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DOI: 10.1246/cl.190467
Abstract: This article describes the development of an iridium-catalyzed reductive nucleophilic addition to tertiary amides. A conspicuous feature of this reaction is its high amide-selectivity via two proce... read more here.
Keywords: iridium catalyzed; tertiary amides; addition tertiary; reductive nucleophilic ... See more keywords