Gold-Catalyzed Hydroamination of Propargylic Alcohols: Controlling Divergent Catalytic Reaction Pathways To Access 1,3-Amino Alcohols, 3-Hydroxyketones, or 3-Aminoketones
نویسندگان
چکیده
منابع مشابه
Facile preparation of allenic hydroxyketones via rearrangement of propargylic alcohols.
[formula: see text] Treatment of tertiary propargylic alcohols 13 with 3-diazo-2-butanone 6 and catalytic dirhodium tetraacetate in benzene gave good yields of the diastereomeric allenic hydroxyketones 14, with, in some cases, good diastereocontrol. These products are presumably formed via the [2,3]-sigmatropic rearrangement of an alpha-propargyloxy enol derivative. This reaction has been exten...
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Hydrozirconation of alkynes with Cp2ZrH(Cl) (Schwartz reagent) generates vinyl zirconium species reliably, stereospecifically, and regioselectively. These organometallic reagents can participate in cross-coupling reactions, conjugate and nucleophilic additions, and can undergo carbonylation and halogenation.1 Hydrozirconation of terminal alkynes often proceeds with >50:1 selectivity to form the...
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Nucleophilic addition to alkynes represents an attractive approach to the synthesis of olefins. Obstacles to this strategy include the low reactivity of alkynes toward many organometallic reagents and difficulties associated with controlling the regioselectivity of addition. Here we demonstrate that Fe(III) salts are effective precatalysts for the carbometalation of alkynes. Primary and seconda...
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The regioselective conversion of propargylic alcohols into previously unreported α,α-diiodo-β-hydroxyketones was achieved by treatment with N-iodosuccinimide in the presence of a gold catalyst. The corresponding α,α-dichloro-β-hydroxyketones were obtained by treatment with trichloroisocyanuric acid in the absence of a catalyst. The latter reaction can be extended to other alkynols. These transf...
متن کاملStereochemical and Skeletal Diversity Arising from Amino Propargylic Alcohols
An efficient synthetic pathway to the possible stereoisomers of skeletally diverse heterocyclic small molecules is presented. The change in shape brought about by different intramolecular cyclizations of diastereoisomeric amino propargylic alcohols is quantified using principal moment-of-inertia (PMI) shape analysis.
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ژورنال
عنوان ژورنال: The Journal of Organic Chemistry
سال: 2019
ISSN: 0022-3263,1520-6904
DOI: 10.1021/acs.joc.9b00988