English (United Kingdom)

https://curated-unify.zendy.io/wp-json/zendy-region/v1/featured_content/oa?rat=en

https://curated-unify.zendy.io/wp-json/zendy-region/v1/highlighted_journal/

Global: Zendy Plus annual

Presents the access of premium content as premium feature

Premium Content

Presents the keyphrase highlighting as premium feature

Keyphrase Highlighting

Presents the summarisation as premium feature

Summarisation

Insights

Presents the pdf analysis as premium feature

PDF Analysis

Presents the zaia usage as premium feature

ZAIA

Global: Zendy Tools annual

Global: Zendy Free Plan

Global: Zendy Tools monthly

Global: Zendy Plus monthly

Significance: Following on their work on DMSOpromoted, Pd(OAc)2-catalyzed allylic oxidation reactions (M. S. Chen, M. C. White J. Am. Chem. Soc. 2004, 126, 1346-1347), the authors proved that no erosion of enantiomeric purity was observed in the course of their methodology when using an enantioenriched alkene (Org. Lett. 2005, 7, 223-226). In the present paper, they describe their recent achievements towards the rapid synthesis of polyol frameworks. In particular, they report on the total synthesis of protected L-galactose. Comment: Initial reaction conditions were carefully optimized to allow the stereoand regioselective allylic oxidation of an a-chiral olefin using panisic acid. Addition of a noncoordinating base and use of phenylbenzoquinone instead of benzoquinone both increased the yield of the reaction. Interestingly, the acetonide protecting group within the chiral moiety proved to be stable under the reaction conditions. The linear product was obtained predominantly over the branched analogue (>300:1) and could be further derivatized to yield the enantioenriched protected L-galactose in five steps. The two remaining stereogenic centers were installed by Sharpless asymmetric dihydroxylation. O OBn

Total Synthesis of Protected l-Galactose by Hydrocarbon Oxidation