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Diastereoselektive Diels‐Alder‐Reaktionen mit α‐Chlornitrososacchariden
Author(s) -
Braun Heinz,
Felber Helena,
Kresze Günter,
Schmidtchen Franz P.,
Prewo Roland,
Vasella Andrea
Publication year - 1993
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199319930146
Subject(s) - chemistry , reagent , enantiomer , oxime , yield (engineering) , diels–alder reaction , absolute configuration , enantiomeric excess , organic chemistry , stereochemistry , enantioselective synthesis , catalysis , materials science , metallurgy
Diastereoselective Diels‐Alder Reactions with α‐Chloronitroso Saccharides The α‐chloronitroso reagent 2 obtained from ribose via the lactone oxime 3 reacts with the dienes 6 – 10 at low temperature to give the chiral dihydrooxazines 11 – 16 in 63–96% yield and > 96% enantiomeric excess. The reagents 1 and 2 which are approximately mirror images in the vicinity of the chloronitroso function lead to opposite enantiomers of 11 – 16 . The absolute configuration of the products was determined by chemical degradation and comparison with authentic amino and hydroxy acids.