Publication | Closed Access
Synthesis of 4-Membered Carbasugars by Way of Stereoselective SmI<sub>2</sub>-Mediated Aldehyde–Alkene Cyclization
23
Citations
31
References
2013
Year
Combinatorial ChemistryBiosynthesisEngineeringAlkene MetathesisBiochemistryStereodivergent SynthesisNatural SciencesMolecular BiologyVitamin COrganic Chemistry4-Membered CarbasugarsStereoselective SynthesisChemistryAldehyde–alkene CyclizationNatural Product SynthesisEnantioselective SynthesisBiomolecular Engineering
A stereodivergent synthesis of the first examples of 4-membered carbasugars has been achieved from vitamin C by way of an efficient intramolecular SmI2-mediated aldehyde-alkene coupling. In this key step, cylobutanes with four contiguous asymmetric centers are generated with a high level of stereocontrol.
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