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On the Asymmetric Induction in Proline‐Catalyzed Aldol Reactions: Reagent‐Controlled Addition Reactions of 2,2‐Dimethyl‐1,3‐dioxane‐5‐one to Acyclic Chiral α‐Branched Aldehydes
Author(s) -
Marjanovic Trajkovic Jasna,
Milanovic Vesna,
Ferjancic Zorana,
Saicic Radomir N.
Publication year - 2017
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.201701073
Subject(s) - aldol reaction , chemistry , reagent , proline , catalysis , asymmetric induction , organic chemistry , aldehyde , organocatalysis , enantioselective synthesis , reaction conditions , combinatorial chemistry , amino acid , biochemistry
Reagent stereocontrol in the proline‐catalyzed aldol reaction of 2,2‐dimethyl‐1,3‐dioxane‐5‐one 1 with chiral aldehydes has been investigated. Synthetically useful levels of diastereoselectivity could be achieved in reactions with acyclic chiral α‐oxy and α‐amino aldehydes in both matched and mismatched cases. By using this reaction as a key step, two medicinally relevant azasugars, 1‐deoxy‐galactonojirimycin ( 9 ) and 2,5‐dideoxy‐2,5‐imino‐ d ‐altritol ( 10 ), were efficiently synthesized.