Tetrahedron p. 3037 - 3043 (1974)
Update date:2022-08-05
Topics:
Naruse
Utimoto
Nozaki
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.
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Doi:10.1055/s-2002-33914
(2002)Doi:10.1016/j.tet.2009.10.035
(2009)Doi:10.1007/s10593-013-1226-0
(2013)Doi:10.1007/s10593-009-0187-9
(2008)Doi:10.1016/S0040-4039(02)02243-8
(2002)Doi:10.1016/S0022-328X(02)01657-1
(2002)
