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Organocatalytic syn ‐Aldol Reactions of Hydroxy Ketones with ( S )‐Isoserinal: Asymmetric Synthesis of 6‐Deoxy‐1,5‐iminohexitols and Related Compounds
Author(s) -
Nicolas Cyril,
Pluta Roman,
PasternakSuder Monika,
Martin Olivier R.,
Mlynarski Jacek
Publication year - 2013
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.201201413
Subject(s) - aldol reaction , chemistry , enantiopure drug , wittig reaction , organocatalysis , enantioselective synthesis , glycoside hydrolase , organic chemistry , catalysis , stereochemistry , combinatorial chemistry , hydrolysis
An improved and convenient preparation of protected ( S )‐isoserinal on a large scale is reported. This key intermediate was reacted through organocatalyzed aldol reaction or Wittig based chain extension and functionalization to give enantiopure 1,5,6‐trideoxy‐1,5‐imino‐hexitols such as 10a ( L ‐ manno ) and 10b ( D ‐ gluco ). These two compounds are of interest as glycosidase inhibitors. The elaborated organocatalytic process includes diastereoselective syn aldol reaction of ( S )‐isoserinal hydrate and hydroxyacetone or 1‐hydroxy‐2‐octanone and is promoted by various amino acid‐based catalysts. Diastereoselectivities of up to 8:1 were achieved, thus establishing a new, efficient synthetic route to these important carbohydrate mimics.