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Enantioselective Synthesis of Monosaccharide Analogues by Two‐Step Sequential Enamine Catalysis: Benzoyloxylation and Aldol Reaction
Author(s) -
Shimogaki Mio,
Takeshima Aika,
Kano Taichi,
Maruoka Keiji
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000073
Subject(s) - enantioselective synthesis , chemistry , aldol reaction , stereocenter , enamine , diastereomer , organocatalysis , monosaccharide , catalysis , organic chemistry , amine gas treating , stereochemistry , combinatorial chemistry
An efficient route to synthesize monosaccharide analogues in an enantio‐ and diastereoselective manner is described. Three contiguous stereocenters can be constructed via enantioselective benzoyloxylation of aldehydes using a chiral secondary amine catalyst and a subsequent aldol reaction of the resulting α ‐benzoyloxyaldehydes with the protected dihydroxyacetones using chiral amino acid catalysts, and single diastereomers were obtained with excellent enantioselectivity.