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Synthese homochiraler 3‐Oxa‐2,7‐diazabicyclo[3.3.0]octane aus Aminosäuren durch intramolekulare 1,3‐dipolare Cycloaddition von Nitronen
Author(s) -
Aurich Hans Günter,
Frenzen Gerlinde,
Gentes Christian
Publication year - 1993
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19931260333
Subject(s) - chemistry , cycloaddition , intramolecular force , octane , nitrone , bicyclic molecule , stereochemistry , 1,3 dipolar cycloaddition , yield (engineering) , medicinal chemistry , organic chemistry , catalysis , materials science , metallurgy
Synthesis of Homochiral 3‐Oxa‐2,7‐diazabicyclo[3.3.0]octanes from Amino Acids by Intramolecular 1,3‐Dipolar Cycloaddition of Nitrones N 1‐Allylamino alcohols 9 were prepared from amino acids by various methods. Swern oxidation of 9 afforded aldehydes 11 . By reaction of 11 with N 1‐alkylhydroxylamines nitrone intermediates 4 were formed which spontaneously underwent an intramolecular 1,3‐dipolar cycloaddition to yield the bicyclic compounds 6 . The cycloaddition proceeds diastereoselectively furnishing homochiral compounds 6 from homochiral starting materials. The structure of 6aA was confirmed by X‐ray structural analysis.