72291-85-1Relevant academic research and scientific papers
Benzoyl Shift: A New Approach to Reverse Regioselectivity in the Monoprotection of vic -Diols
De La Torre, Aurélien,Oger, Camille,Bultel-Poncé, Valérie,Durand, Thierry,Galano, Jean-Marie
, p. 2205 - 2208 (2016/11/07)
The benzoyl shift in monoprotected vic-diols is described. Triggered under mild conditions, this transformation allows regioselective protection of the least acidic hydroxyl function of an activated vic-diol.
Practical one-pot sequence for the asymmetric synthesis of 1,2 diols from primary alcohols
Hermange, Philippe,Portalier, Fran?ois,Thomassigny, Christine,Greck, Christine
, p. 1052 - 1055 (2013/04/10)
A practical one-pot three-step sequence is reported for the asymmetric synthesis of α-benzoyloxylated alcohols from primary alcohols. Good overall yields (36-52%) and enantioselectivities (91-94% e.e.) are obtained using a commercial organocatalyst in the key oxylation reaction. A simple modification in the protocol allows the formation of enantioenriched γ-benzoyloxylated α,β-unsaturated ester from alcohol. Synthetic utility has been harnessed to the easy preparation of (-)-γ-octalactone from hexan-1-ol.
