The First Boron-Tethered Radical Cyclizations and Intramolecular Homolytic Substitutions at Boron

The First Boron-Tethered Radical Cyclizations and Intramolecular Homolytic Substitutions at Boron

5‐, 6‐, and even 7‐exo‐trig radical cyclizations (1→2) are possible by applying a new boron‐tethering approach with alkenylboronic esters. For certain substitution patterns, a subsequent intramolecular homolytic substitution (SHi) reaction at boron occurs (2→3) and leads to rearranged products. The...

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Veröffentlicht in:Angewandte Chemie International Edition 1999-06, Vol.38 (12), p.1798-1800
Hauptverfasser: Batey, Robert A., Smil, David V.
Format: Artikel
Sprache:eng
Schlagworte:
Boron
Cyclizations
Radical reactions
Rearrangements
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Zusammenfassung:5‐, 6‐, and even 7‐exo‐trig radical cyclizations (1→2) are possible by applying a new boron‐tethering approach with alkenylboronic esters. For certain substitution patterns, a subsequent intramolecular homolytic substitution (SHi) reaction at boron occurs (2→3) and leads to rearranged products. The C−B bond of the intermediate boracycles is readily oxidized to give diol products.
ISSN:1433-7851
1521-3773
DOI:10.1002/(SICI)1521-3773(19990614)38:12<1798::AID-ANIE1798>3.0.CO;2-0