155433-74-2Relevant academic research and scientific papers
Stereoselective Synthesis of Alcohols, XLIV. Cyclization of Benzyloxy-Substituted (8-Oxo-2-octenyl)boronates
Sander, Thomas,Hoffmann, Reinhard W.
, p. 1193 - 1200 (2007/10/02)
The cyclization of (8-oxo-2-octenyl)boronates having benzyloxy substituents in the chain linking the two functional groups gives benzyloxy-substituted 2-vinylcyclohexanols.High asymmetric induction is found for the 4- or 6-benzyloxy-(Z)-octenylboronates 12a and 12c, whereas cyclization of the other isomers studied proceeded in a stereorandom fashion.Possible reasons for this unexpected behavior are discussed. - Key Words: Cyclization, stereoselective / Allylboration, intramolecular / Transition state conformations, polar effects on / Boronates
