A historical overview is presented on stereo-directing effects of cis- and trans-fused diol protective groups used on both donor and acceptor glycosides. Attention is focused on the use of cyclic carbonates and carbamates, diacetals and acetals and finally the special case of 1,2-O-orthoesters and 1,2-O-cyanoalkylidene functionalised residues.
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http://dx.doi.org/10.1016/j.carres.2006.09.002 | DOI Listing |
J Am Chem Soc
January 2025
Department of Chemistry, University of Wisconsin─Madison, 1101 University Avenue, Madison, Wisconsin 53706, United States.
Hydrazides are known to catalyze reactions of α,β-unsaturated aldehydes via transient iminium formation. The iminium intermediate displays enhanced electrophilicity, which facilitates conjugate additions and cycloadditions. We observed that a hydrazide embedded in a seven-membered ring catalyzes homoaldol condensation of a simple aldehyde in a process that displays an approximate second-order dependence on the hydrazide.
View Article and Find Full Text PDFJ Agric Food Chem
January 2025
Key Laboratory of Industrial Fermentation Microbiology (Ministry of Education), Tianjin University of Science & Technology, Tianjin 300457, People's Republic of China.
Nature
January 2025
Department of Chemistry, The Scripps Research Institute, La Jolla, CA, USA.
C-H activation is the most direct way of functionalizing organic molecules. Many advances in this field still require specific directing groups to achieve the necessary activity and selectivity. Developing C-H activation reactions directed by native functional groups is essential for their broad application in synthesis.
View Article and Find Full Text PDFJ Colloid Interface Sci
December 2024
Laboratory of Alternative Energy Conversion Systems, Department of Mechanical Engineering, School of Engineering, University of Thessaly, Pedion Areos 38834, Greece. Electronic address:
The coupling of carbon dioxide (CO) with epoxides to produce cyclic carbonates is a desirable decarbonization approach, but its commercial applicability is still restricted by the costly catalysts required, as well as the need for high temperature and high pressure. Herein, oxygen vacancy-rich defective tungsten oxide (WO) rich in Lewis acid sites was modified by Prussian blue (PB), and the obtained composite reaches up to 94 % styrene carbonate yield (171 mmol gh) at ambient temperature and pressure, exhibiting outstanding advantages in the photocatalytic CO cycloaddition reaction compared with currently reported photocatalysts. It is found that the introduction of PB with photothermal properties significantly enhances the capability of WO to absorb and activate CO and epoxide, along with its light utilization ability.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
State Key Laboratory Materials-Oriented Chemical Engineering, College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, 30 Puzhu Road South, Nanjing 211816, China.
The cycloaddition of CO to epoxide (CCE) reactions produce valuable cyclic carbonates useful in the electrolytes of lithium-ion batteries, as organic solvents, and in polymeric materials. However, halide-containing catalysts are predominantly used in these reactions, despite halides being notoriously corrosive to steel processing equipment and residual halides also having harmful effects. To eliminate the reliance on halides as cocatalyst in most CCE reactions, halide-free catalysts are highly desirable.
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