Synthesis of tertiary 1,3-butadien-2-ylcarbinols from chromium-catalyzed addition of (4-bromobut-2-ynyl)trimethylsilane to ketones
The synthesis of 1,3-butadien-2-ylcarbinols containing a tertiary alcohol is achieved by desilylation of (trimethylsilyl)methylallenic alcohols. The latter are obtained via a chromium-catalyzed addition of (4-bromobut-2-ynyl) trimethylsilane to aliphatic or aromatic ketones. The desired adducts are obtained in yields ranging from 21% to 67% for this two-step, one-pot process.
Durán-Galván, María,Hemmer, James R.,Connell, Brian T.
supporting information; experimental part
p. 5080 - 5082
(2011/01/12)
A Convenient Route to 2-Lithio-1,3-butadiene from Chloroprene via 2-Stannyl-1,3-butadiene
A convenient route to 2-lithio-1,3-butadiene from chloroprene via a 2-stannyl-1,3-butadiene is presented, and the regioselective additions to a variety of carbonyl groups are demonstrated.