Hydroxy Group-directed Diastereoselective Paternò-Büchi Reaction between Arylglyoxylates and Furfuryl Alcohols

A hydroxy group-directed Paternò-Büchi (PB) reaction between arylglyoxylates and furfuryl alcohols afforded the corresponding oxetanes regio- and diastereoselectively. Furthermore, the PB reaction between β-naphthylglyoxylate possessing diisopropyl (R,R)-tartrate moiety and furfuryl alcohol achieved...

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Bibliographic Details
Published in:Chemistry letters 2022-12, Vol.51 (12), p.1143-1145
Main Authors: Wei, Qi, Ii, Hiromi, Suga, Takuya, Soeta, Takahiro, Maeda, Hajime, Ukaji, Yutaka
Format: Article
Language:eng ; jpn
Subjects:
Furfuryl alcohol
Stereoselectivity
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Summary:A hydroxy group-directed Paternò-Büchi (PB) reaction between arylglyoxylates and furfuryl alcohols afforded the corresponding oxetanes regio- and diastereoselectively. Furthermore, the PB reaction between β-naphthylglyoxylate possessing diisopropyl (R,R)-tartrate moiety and furfuryl alcohol achieved high chiral induction to produce the corresponding optically pure oxetane after the removal of the chiral auxiliary.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.220437