Palladium-catalyzed conjunctive cross-coupling can be accomplished with the use of chiral phosphine-oxazoline based ligand structures. Of note, the reaction can be conducted on Grignard-based boron ate complexes and operates without the use of halide-scavenging additives, which are required for other catalyst systems.
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http://dx.doi.org/10.1021/acs.joc.2c02341 | DOI Listing |
Adv Carbohydr Chem Biochem
November 2024
Department of Chemistry and Chemical Biology, Northeastern University, Boston, Massachusetts, USA.
The various methods for the de novo asymmetric synthesis of the pyranose sugars are surveyed in this update of the 2013 Advances in Carbohydrate Chemistry and Biochemistry review. The survey begins with a general overview of the various de novo approaches to carbohydrates and defines the use of asymmetric catalysis for the de novo asymmetric synthesis of pyranoses. Next the application to pyranose-containing oligosaccharides is introduced via the use of a palladium-mediated glycosylation.
View Article and Find Full Text PDFJ Org Chem
February 2023
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, United States.
Palladium-catalyzed conjunctive cross-coupling can be accomplished with the use of chiral phosphine-oxazoline based ligand structures. Of note, the reaction can be conducted on Grignard-based boron ate complexes and operates without the use of halide-scavenging additives, which are required for other catalyst systems.
View Article and Find Full Text PDFChem Commun (Camb)
November 2022
Department of Chemistry and Chemical Biology, Northeastern University, Boston, MA, 02115, USA.
The development and application of the asymmetric synthesis of oligosaccharides from achiral starting materials is reviewed. This asymmetric approach centers around the use of asymmetric catalysis for the synthesis of optically pure furan alcohols in conjunction with Achmatowicz oxidative rearrangement for the synthesis of various pyranones. In addition, the use of a diastereoselective palladium-catalyzed glycosylation and subsequent diastereoselective post-glycosylation transformation was used for the synthesis of oligosaccharides.
View Article and Find Full Text PDFAcc Chem Res
February 2022
Department of Chemistry, The Scripps Research Institute, 10550 N. Torrey Pines Road, La Jolla, California 92037, United States.
Enolate alkylation and conjugate addition into an α,β-unsaturated system have served as long-standing strategic disconnections for the installation of α- or β-substituents on carbonyl-containing compounds. At the onset of our efforts to develop C-H activation reactions for organic synthesis, we set our eye toward developing asymmetric β-C-H activation reactions of aliphatic acids with the perspective that this bond-forming event could serve as a more flexible retrosynthetic surrogate for both canonical carbonyl-related asymmetric transformations.In this Account, we describe our early efforts using strongly coordinating chiral oxazolines to probe reaction mechanism and the stereochemical nature of the C-H cleavage transition state.
View Article and Find Full Text PDFAcc Chem Res
August 2020
Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565-0871, Japan.
Aziridines, i.e., the smallest saturated N-heterocycles, serve as useful building blocks in synthetic organic chemistry.
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