New tandem Zn-promoted Brook rearrangement/ene-allene carbocyclization reactions.
[reaction: see text] A new tandem reaction was developed for the carbocyclization reaction of propargylic zinc reagents. First, we have shown that zinc salt promotes the Brook rearrangement into the carbanionic species followed by a stereospecific Zn-ene-allene carbocyclization reaction to lead to the corresponding cyclopentylmethylzinc derivatives. A single diastereoisomer is formed, even when a tertiary and a quaternary center are linked in the process.
Unger
Rozalia
R
The Mallat Family Laboratory of Organic Chemistry, Department of Chemistry, Institute of Catalysis Science and Technology, Technion-Israel Institute of Technology, Technion City, Haifa 32000, Israel.
Cohen
Theodore
T
Marek
Ilan
I