Reagent-Controlled Regiodivergent Annulations of Achmatowicz Products with Vinylogous Nucleophiles: Synthesis of Bicyclic Cyclopenta[b]pyrans and 8-Oxabicyclo[3.2.1]octane Derivatives.
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DOI: 10.1021/acs.orglett.2c03127
Abstract: Two reagent-controlled regiodivergent annulation protocols for Achmatowicz products with vinylogous nucleophiles have been developed, which furnished a series of bicyclic cyclopenta[b]pyrans and 8-oxabicyclo[3.2.1]octane derivatives in 28-90% yields. Plausible mechanisms were proposed to involve either Pd-catalyzed… read more here.
Keywords: bicyclic cyclopenta; products vinylogous; controlled regiodivergent; achmatowicz products ... See more keywords
Ligand-Controlled Regiodivergent Hydroformylation of Ynamides: A Stereospecific and Regioselective Access to 2- and 3-Aminoacroleins.
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DOI: 10.1021/acs.orglett.9b03566
Abstract: The rhodium-catalyzed hydroformylation of ynamides is described and gives selective access to 2- or 3-aminoacrolein derivatives. The regioselectivity of this carbonylation can be completely controlled at will thanks to the nature of the ligand used.… read more here.
Keywords: hydroformylation ynamides; hydroformylation; controlled regiodivergent; ligand controlled ... See more keywords
Ligand-Controlled Regiodivergent Silylation of Allylic Alcohols by Ni/Cu Catalysis for the Synthesis of Functionalized Allylsilanes.
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DOI: 10.1021/acs.orglett.9b03822
Abstract: The first Ni/Cu-catalyzed regiodivergent synthesis of allylsilanes directly from allylic alcohols through modulating the steric and electronic properties of the ligands on the nickel catalyst has been developed. Good yields and excellent selectivity were obtained… read more here.
Keywords: regiodivergent silylation; controlled regiodivergent; allylic alcohols; silylation allylic ... See more keywords
Reagent-controlled regiodivergent ring expansions of steroids
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DOI: 10.1038/s41467-018-03248-2
Abstract: Ring expansion provides a powerful way of introducing a heteroatom substituent into a carbocyclic framework. However, such reactions are often limited by the tendency of a given substrate to afford only one of the two… read more here.
Keywords: late stage; reagent controlled; ring expansion; natural products ... See more keywords
Ligand-controlled regiodivergent aminocarbonylation of cyclobutanols toward 1,1- and 1,2-substituted cyclobutanecarboxamides
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DOI: 10.1038/s41467-024-53571-0
Abstract: Four-membered carbocycles are among the most sought-after backbones which are commonly found in biologically active molecules. However, difficulties on their producing are existing due to its highly strained ring system. On the other hand, cyclobutanols… read more here.
Keywords: controlled regiodivergent; ligand controlled; cyclobutanols toward; aminocarbonylation cyclobutanols ... See more keywords
Ligand-controlled regiodivergent π-allyl palladium catalysis enables a switch between [3+2] and [3+3] cycloadditions.
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DOI: 10.1039/c9cc00611g
Abstract: Reported herein is the use of ligands to tune the regioselectivity and reactivity of palladium-catalyzed [3+2] and [3+3] cycloadditions. Diverse synthesis with vinylethylene carbonates (VECs) as well as free naphthols has been explored to construct… read more here.
Keywords: regiodivergent allyl; controlled regiodivergent; palladium catalysis; ligand controlled ... See more keywords
Ligand-controlled regiodivergent Ni-catalyzed trans-hydroboration/carboboration of internal alkynes with B2pin2
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DOI: 10.1039/d3sc04184k
Abstract: Unprecedented regioselective trans-hydroboration and carboboration of unbiased electronically internal alkynes were realized via a nickel catalysis system with the aid of the directing group strategy. Furthermore, the excellent α- and β-regioselectivity could be accurately switched… read more here.
Keywords: controlled regiodivergent; ligand controlled; trans hydroboration; hydroboration carboboration ... See more keywords