3-Chloro-1-lithiopropene, a Functional Organolithium Reagent, and Its Reactions with Alkylboronates To Give 3-Alkylprop-1-en-3-ols

Citations Over TimeTop 20% of 2013 papers

Abstract

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.

Related Papers

• → Transition metal-catalyzed allylic substitution reactions with unactivated allylic substrates(2015)668 cited
• → Metal-catalyzed rearrangements of allylic esters(1984)59 cited
• → One-Pot Synthesis of Homoallylic Alcohols via a Facile Conversion of Allylic Alcohols into Allylic Iodides(1989)30 cited
• Synthesis and reactions of organic compounds with a nitrogen atom. Part XVI. Reactions of (-)-4-chloro-3(10)-carene and(+)-10-chloro-3-carene with phenyltelluro- andc phenylselenosodium(1999)
• → ChemInform Abstract: Allylic Selenides in Organic Synthesis: New Methods for the Synthesis of Allylic Amines.(1987)