Chelation control in the [3 + 3] annulation reaction of alkoxy-substituted 1,1-diacylcyclopropanes with 1,3-bis(trimethylsilyloxy)-1,3-butadienes. diversity-oriented synthesis of isochromanes.
Functionalized arenes were prepared by chelation-controlled [3 + 3] cyclization/cyclopropane opening reactions of 1-trimethylsilyloxy-1,3-butadienes with benzyloxy- or methoxy-substituted 1,1-diacylcyclopropanes. A number of benzyloxy-substituted derivatives were transformed into isochromanes by deprotection and subsequent cyclization. Mixed chromanes-isochromanes were prepared starting with 1,3-bis(silyloxy)-1,3-butadienes containing a remote chloride group.
Karapetyan
Vahuni
V
Institut fr Chemie der Universität Rostock, Albert-Einstein-Strasse 3a, D-18059 Rostock, Germany.
Mkrtchyan
Satenik
S
Hefner
Jennifer
J
Fischer
Christine
C
Langer
Peter
P
D002070:Butadienes / Q000737:chemistry*; D002384:Catalysis; D002614:Chelating Agents / Q000737:chemistry*; D002839:Chromans / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D003521:Cyclopropanes / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
D002070:Butadienes; D002614:Chelating Agents; D002839:Chromans; D003521:Cyclopropanes; D014297:Trimethylsilyl Compounds