Unknown

Dataset Information

0

Hypervalent iodine(III)-promoted intermolecular C-C coupling of vindoline with ?-ketoesters and related substrates.

ABSTRACT: The regioselective intermolecular coupling reaction of vindoline with a wide range of substrates including ?-ketoesters, ?-diketones, ?-ketoaldehydes, ?-ketonitriles, malononitriles, and ?-cyanoesters provides an opportunity for the synthesis of vinblastine analogues containing deep-seated changes in the upper velbanamine subunit. The transition-metal-free hypervalent iodine(III)-promoted intermolecular sp(3)/sp(2) coupling, representing a special class of selective C-H activation with direct carbon-carbon bond formation, proceeds with generation of a quaternary center capable of incorporation of the vinblastine C16' methyl ester and functionalized for subsequent divergent heterocycle introduction.

SUBMITTER: Turner TC 

PROVIDER: S-EPMC3607625 | biostudies-literature | 2013 Mar

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Hypervalent iodine(III)-promoted intermolecular C-C coupling of vindoline with β-ketoesters and related substrates.

Turner Travis C TC   Shibayama Kotaro K   Boger Dale L DL  

Organic letters 20130219 5

The regioselective intermolecular coupling reaction of vindoline with a wide range of substrates including β-ketoesters, β-diketones, β-ketoaldehydes, β-ketonitriles, malononitriles, and β-cyanoesters provides an opportunity for the synthesis of vinblastine analogues containing deep-seated changes in the upper velbanamine subunit. The transition-metal-free hypervalent iodine(III)-promoted intermolecular sp(3)/sp(2) coupling, representing a special class of selective C-H activation with direct ca  ...[more]

Similar Datasets

Unknown Hypervalent Iodine(III)-Promoted C3-H Regioselective Halogenation of 4-Quinolones under Mild Conditions.
| S-EPMC8675166 | biostudies-literature
Unknown A Benziodoxole-Based Hypervalent Iodine(III) Compound Functioning as a Peptide Coupling Reagent.
| S-EPMC7093377 | biostudies-literature
Unknown Rapid transformation of sulfinate salts into sulfonates promoted by a hypervalent iodine(III) reagent.
| S-EPMC6009181 | biostudies-other
Unknown Structurally Defined Molecular Hypervalent Iodine Catalysts for Intermolecular Enantioselective Reactions.
| S-EPMC4832830 | biostudies-other
Unknown Chiral Hypervalent Iodine Catalysis Enables an Unusual Regiodivergent Intermolecular Olefin Aminooxygenation.
| S-EPMC8243328 | biostudies-literature
Unknown Hypervalent Iodine(III)-Catalysed Enantioselective ?-Acetoxylation of Ketones.
| S-EPMC7496773 | biostudies-literature
Unknown Hypervalent Iodine(III) Compounds as Biaxial Halogen Bond Donors.
| S-EPMC7252947 | biostudies-literature
Unknown Enantioselective dioxytosylation of styrenes using lactate-based chiral hypervalent iodine(III).
| S-EPMC5870148 | biostudies-literature
Unknown Visible-Light, Iodine-Promoted Formation of N-Sulfonyl Imines and N-Alkylsulfonamides from Aldehydes and Hypervalent Iodine Reagents.
| S-EPMC6222766 | biostudies-other
Unknown Hypervalent iodine(III)-mediated decarboxylative acetoxylation at tertiary and benzylic carbon centers.
| S-EPMC6009488 | biostudies-literature