Stereoselective synthesis of alcohols, XL. Stereoselective cyclization of 7??oxo??2??heptenylboronates
RW Hoffmann, G Niel
Index: Hoffmann, Reinhard W.; Niel, Gilles Liebigs Annalen der Chemie, 1991 , # 11 p. 1195 - 1201
Full Text: HTML
Citation Number: 11
Abstract
Abstract Intramolecular allylboration reaction of 7-oxo-2-heptenyl boronates leads to 2- vinylcyclopentanols. The cyclization proceeds in a stereospecific manner, such that the (E)- allylboronate 8 is converted into trans-2-vinylcyclopentanol (2) and the (Z)-allylboronate 10 into cis-2-vinylcyclopentanol (3). Asymmetric induction originating from stereogenic centers placed between the boronate and the aldehyde function has been found to be low.
Related Articles:
Functional??Group??Tolerant Catalytic Migratory Oxidative Coupling of Nitrones
[Hashizume, Shogo; Oisaki, Kounosuke; Kanai, Motomu Chemistry - An Asian Journal, 2012 , vol. 7, # 11 p. 2600 - 2606,7]