Access to enantioenriched 2,3- and 2,5-dihydrofurans with a fully substituted C2 stereocenter by Pd-catalyzed asymmetric intermolecular Heck reaction
نویسندگان
چکیده
منابع مشابه
Access to enantioenriched 2,3- and 2,5-dihydrofurans with a fully substituted C2 stereocenter by Pd-catalyzed asymmetric intermolecular Heck reaction† †Electronic supplementary information (ESI) available: Experimental procedures, characterization of all new compounds, VCD studies and spectral data. See DOI: 10.1039/c5sc01460c Click here for additional data file.
During the past decades, building on the seminal contributions of Overman and Shibasaki, the asymmetric intramolecular Heck reaction has been successfully applied in natural product synthesis to install tertiary and quaternary stereocenters. In stark contrast, the intermolecular version of this asymmetric transformation has not reached the same level of development and its synthetic utility rem...
متن کاملPalladium-catalyzed intermolecular Heck reaction of alkyl halides.
Intermolecular Heck reaction of common alkyl halides, a longstanding problem in palladium catalysis, is realized with a simple Pd/dppf catalyst. Both primary and secondary alkyl halides are suitable for coupling with aromatic olefins. Single electron transfer from (dppf)Pd(0) to alkyl halide initiated the catalytic cycle and gave alkyl radicals.
متن کاملPhosphite-oxazole/imidazole ligands in asymmetric intermolecular Heck reaction.
We describe the application of a new class of ligands--the phosphite-oxazole/imidazole (L1-L5a-g)--in asymmetric intermolecular Pd-catalyzed Heck reactions under thermal and microwave conditions. These ligands combine the advantages of the oxazole/imidazole moiety with those of the phosphite moiety: they are more stable than their oxazoline counterparts, less sensitive to air and other oxidizin...
متن کاملEndo-Selective Pd-Catalyzed Silyl Methyl Heck Reaction
A palladium (Pd)-catalyzed endo-selective Heck reaction of iodomethylsilyl ethers of phenols and aliphatic alkenols has been developed. Mechanistic studies reveal that this silyl methyl Heck reaction operates via a hybrid Pd-radical process and that the silicon atom is crucial for the observed endo selectivity. The obtained allylic silyloxycycles were further oxidized into (Z)-alkenyldiols.
متن کاملCopper(I)-Catalyzed Multicomponent Reaction Providing a New Access to Fully Substituted Thiophene Derivatives
Readily available triethylammonium 1-(2-oxoindolin-3-ylidene)-2-aroylethanethiolates are efficiently converted into a variety of fully substituted thiophene derivatives by copper(I)-catalyzed denitrogenative reactions with terminal alkynes and N-sulfonyl azides. This new reaction simultaneously installs C-N, C-S, and C-C bonds, allowing direct formation of highly functionalized thiophenes with ...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
ژورنال
عنوان ژورنال: Chemical Science
سال: 2015
ISSN: 2041-6520,2041-6539
DOI: 10.1039/c5sc01460c