- Alkenyl Isocyanide Conjugate Additions: A Rapid Route to γ-Carbolines
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Isocyanides are exceptional building blocks, the wide deployment of which in multicomponent and metal-insertion reactions belies their limited availability. The first conjugate addition/alkylation to alkenyl isocyanides is described, which addresses this deficiency. An array of organolithiums, magnesiates, enolates, and metalated nitriles add conjugately to β- and β,β-disubstituted arylsulfonyl alkenyl isocyanides to rapidly assemble diverse isocyanide scaffolds. The intermediate metalated isocyanides are efficiently trapped with electrophiles to generate substituted isocyanides incorporating contiguous tri- and tetra-substituted centers. The substituted isocyanides are ideally functionalized for elaboration into synthetic targets as illustrated by the three-step synthesis of γ-carboline N-methyl ingenine B.
- Chepyshev, Sergiy V.,Lujan-Montelongo, J. Armando,Chao, Allen,Fleming, Fraser F.
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p. 4310 - 4313
(2017/04/04)
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- 1-Trifluoromethylisoquinolines from α-Benzylated Tosylmethyl Isocyanide Derivatives in a Modular Approach
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The preparation of various 1-trifluoromethylisoquinolines from α-benzylated tosylmethyl isocyanide derivatives and the commercial Togni reagent using a radical cascade is reported. The starting isocyanides are readily prepared in a modular sequence from commercial tosylmethyl isocyanide via sequential double α-alkylation, and the radical reaction proceeds under mild conditions with high efficiency without any transition-metal catalyst via electron catalysis. This valuable protocol has been successfully applied to the total synthesis of CF3-mansouramycin B.
- Wang, Lin,Studer, Armido
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supporting information
p. 5701 - 5704
(2017/10/25)
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- Sulfination of Alcohols with p-Toluenesulfonylmethyl Isocyanide under Metal-Free Conditions: A Mitsunobu Approach
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A Mitsunobu approach for the synthesis of sulfinate esters by direct nucleophilic substitution of alcohols is described. The salient features of this strategy include neutral and metal-free conditions for the rapid synthesis of sulfinates in high yields. The present protocol using p-toluenesulfonylmethyl isocyanide (TosMIC) and the triphenylphosphine (TPP)/diisopropyl azodicarboxylate (DIAD) reagent system represents the general synthetic route to this important class of compounds. (Figure presented.).
- Kadari, Lingaswamy,Radha Krishna, Palakodety,Lakshmi Prapurna
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supporting information
p. 3863 - 3868
(2016/12/16)
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- Discovery of a type III inhibitor of LIM kinase 2 that binds in a DFG-out conformation
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The first allosteric, type III inhibitor of LIM-kinase 2 (LIMK2) is reported. A series of molecules that feature both an N-phenylsulfonamide and tertiary amide were not only very potent at LIMK2 but also were extremely selective against a panel of other k
- Goodwin, Nicole C.,Cianchetta, Giovanni,Burgoon, Hugh A.,Healy, Jason,Mabon, Ross,Strobel, Eric D.,Allen, Jason,Wang, Shuli,Hamman, Brian D.,Rawlins, David B.
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supporting information
p. 53 - 57
(2017/01/18)
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- Discovery of a Type III Inhibitor of LIM Kinase 2 That Binds in a DFG-Out Conformation
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The first allosteric, type III inhibitor of LIM-kinase 2 (LIMK2) is reported. A series of molecules that feature both an N-phenylsulfonamide and tertiary amide were not only very potent at LIMK2 but also were extremely selective against a panel of other k
- Goodwin, Nicole C.,Cianchetta, Giovanni,Burgoon, Hugh A.,Healy, Jason,Mabon, Ross,Strobel, Eric D.,Allen, Jason,Wang, Shuli,Hamman, Brian D.,Rawlins, David B.
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supporting information
p. 53 - 57
(2015/01/30)
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- One-pot Van Leusen synthesis of 4,5-disubstituted oxazoles in ionic liquids
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An efficient and mild protocol for the preparation of 4,5-disubstituted oxazoles through an improved one-pot van Leusen oxazole synthesis in ionic liquids is described. The oxazole products were prepared from tosylmethyl isocyanide (TosMIC), aliphatic hal
- Wu, Bo,Wen, Jun,Zhang, Ji,Li, Jing,Xiang, Yong-Zhe,Yu, Xiao-Qi
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experimental part
p. 500 - 504
(2009/08/07)
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