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Stereodivergent De Novo Synthesis of Branched Amino Sugars by Lewis Acid Promoted Rearrangement of 1,2‐Oxazines
Author(s) -
Pfrengle Fabian,
Lentz Dieter,
Reißig HansUlrich
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200805724
Subject(s) - oxazines , chemistry , sugar , lewis acids and bases , bicyclic molecule , amino acid , stereochemistry , organic chemistry , catalysis , biochemistry
Well concealed : 1,2‐oxazines such as 1 rearrange under Lewis acidic conditions to bicyclic products of type 2 , which can be incorporated into oligosaccharides as protected amino sugar equivalents. Subsequent reductive steps provide unusual oligosaccharides 3 having C2‐branched 4‐amino sugar units. Most of the reactions proceed with excellent stereocontrol and allow the synthesis of a collection of stereoisomers.