37675-31-3Relevant academic research and scientific papers
3-Chloro-1-lithiopropene, a functional organolithium reagent, and its reactions with alkylboronates to give 3-alkylprop-1-en-3-ols
Smith, Keith,Elliott, Mark C.,Jones, D. Heulyn
, p. 9526 - 9531 (2013/10/08)
The reagent 3-chloro-1-lithiopropene (4) can be generated by treating 1-bromo-3-chloropropene with t-BuLi. It is unstable but if generated at low temperature in the presence of alkylboronic esters, such as 3, is trapped in situ to give rearrangement products 2, which on oxidation give 3-alkylprop-1-en-3-ols in good yields. The reaction works for primary, secondary, benzylic, and even tertiary alkylboronic esters, providing allylic alcohols bearing almost any alkyl group available using organoborane chemistry and incorporating all features of such groups.
Synthesis of γ-functionalized allyltrichlorosilanes and their application in the asymmetric allylation of aldehydes
Malkov, Andrei V.,MacDonald, Claire,Koovsky, Pavel
scheme or table, p. 1173 - 1175 (2010/11/02)
Isomerically pure trans-and cis-γ-bromoallyltrichlorosilanes 4 and 5 have been synthesized and shown to react with aromatic aldehydes 1 in the presence of Lewis-basic catalysts (e.g., DMF) to produce the corresponding anti-and syn-allylbromohydrins 8 and 9, respectively, as single diastereoisomers. With BINAPO 25 as a chiral catalyst, promising enantioselectivity (≤50% ee) has been attained.
