Divergent Synthesis of Dihydropyranone Stereoisomers via N‐Heterocyclic Carbene Catalysis. Issue 7 (12th February 2019)

• Record Type: Journal Article
• Authors: Zhao, Changgui; Wang, Jian
• Is Part Of: Advanced synthesis & catalysis. Volume 361:Issue 7(2019)
• Page Start: 1668
• Page End: 1672
• Publication Date: 2019-02-12
• Subjects: carbohydrates -- lactols -- asymmetric catalysis -- N-heterocyclic carbenes -- divergent Achmatowicz rearrangement; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201801639
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: We recently developed a novel chiral N‐heterocyclic carbene (NHC) catalyzed dynamic kinetic enantioselective acylation (DKEA) and dynamic kinetic diastereoselective acylation (DKDA) of Achmatowicz rearrangement products to generate useful intermediates for the further synthesis of carbohydrates. In this update, we describe a divergent NHC catalytic strategy for the stereoselective preparation of all four isomers starting from a common racemic precursor. The present report provides easy access to diverse optically pure dihydropyranones. Abstract :