Cascade Reactions with Chiral Michael Acceptors; Synthesis of Enantiomerically Pure Tricyclo[3.2.1.0]- and Bicyclo[3.2.1]octanes

Publication Type
Journal contribution
Authors
Braun, N. A.; Klein, I.; Spitzner, D.;Vogler B.; Braun, S.; Borrmann, H.; Simon, A.
Year of publication
1995
Published in
Tetrahedron Letters
Band/Volume
1995/nnb
Page (from - to)
2165-2169
Abstract

Starting from the easily accessible (2R)-2,3-O-isopropylideneglyceraldehyde, enantiomerically pure (Z)- and (E)-chloro-unsatd. esters I were obtained in good yields by olefination reactions. (Z)- and (E)-I were allowed to react with kinetically control-generated deprotonated 3-benzyloxycyclohex-2- enone to give enantiomerically pure tricyclooctane II and its enantiomer, resp. The 'push-pull' substituted cyclopropane moiety of II was opened to give solely the bicyclooctane III.

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