49580-86-1Relevant articles and documents
The reaction of lithium trialkylalkynylborates with oxiranes. γ-Hydroxyketone synthesis and stereoselective preparation of trisubstituted ethylenes
Naruse,Utimoto,Nozaki
, p. 3037 - 3043 (1974)
Lithium trialkylalkynylborates (1) react with oxiranes (2) to give non-isolable intermediates 3 which subsequently afford either γ-hydroxyketones 5, trisubstituted ethylenes of homoallylic alcohol type 6 or a tetrasubstituted ethylene 7 upon appropriate treatment with NaOH/H2O2, AcOH or NaOH/I2, respectively. The reaction of oxiranes with 1 proceeds in high regioselectivity and the resulting homoallylic alcohols 6 are of nearly 100% (E) configuration. A straight chain γ-hydroxyketone 16 is obtained in the reaction of methyloxirane with the ate-complex (1), which has been prepared from lithium acetylide ethylenediamine complex and trihexylborane.
