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Enantiomerenreine 3,7‐Dioxa‐2‐azabicylo[3.3.0]octane durch intramolekulare 1,3‐dipolare Cycloaddition von Nitronen
Author(s) -
Güinter Aurich Hans,
Biesemeie Frank,
Boutahar Mostafa
Publication year - 1991
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.19911241028
Subject(s) - chemistry , cycloaddition , diastereomer , intramolecular force , bicyclic molecule , octane , tetrahydrofuran , medicinal chemistry , stereochemistry , 1,3 dipolar cycloaddition , organic chemistry , catalysis , solvent
Enantiomerically Pure 3,7‐Dioxa‐2‐azabicyclo[3.3.0]octanes by Intramolecular 1,3‐Dipolar Cycloaddition of Nitrones Starting with chiral non‐racemic esters of lactic acid 7 and mandelic acid 8 , respectively, chiral nitrones 4 have been prepared. They spontaneously undergo an intramolecular cycloaddition which proceeds with asymmetric induction by the chiral center yielding exclusively the bicyclic compounds 5 in enantimerically pure form. Reductive opening of the isoxazolidine ring affords tetrahydrofuran derivatives 13 with an γ‐amino alcohol group. Reaction of 13 with (‐)‐camphanoyl chloride gives the esters 14. Their 1 H‐NMR spectra reveal a diastereomeric purity of at least 98%.