Cu-Catalyzed Asymmetric Borylative Cyclization of
Cyclohexadienone-Containing 1,6-Enynes
Ping Liu
Yuki Fukui
Ping Tian
Zhi-Tao He
Cai-Yun Sun
Nuo-Yi Wu
Guo-Qiang Lin
10.1021/ja404593c.s001
https://acs.figshare.com/articles/journal_contribution/Cu_Catalyzed_Asymmetric_Borylative_Cyclization_of_Cyclohexadienone_Containing_1_6_Enynes/2387089
The
first Cu-catalyzed asymmetric borylative cyclization of cyclohexadienone-containing
1,6-enynes is achieved through a tandem process: selective β-borylation
of propargylic ether and subsequent conjugate addition to cyclohexadienone.
The reaction proceeds with excellent regioselectivity and enantioselectivity
to afford an optically pure <i>cis</i>-hydrobenzofuran framework
bearing alkenylboronate and enone substructures. Furthermore, the
resulting bicyclic products could be converted to bridged and tricyclic
ring structures. This method extends the realm of Cu-catalyzed asymmetric
tandem reactions using bis(pinacolato)diboron (B<sub>2</sub>pin<sub>2</sub>).
2013-08-14 00:00:00
enantioselectivity
propargylic ether
tandem reactions
enone substructures
Cyclization
alkenylboronate
tricyclic ring structures
enyne
regioselectivity
realm
Asymmetric
conjugate addition
EnynesThe
bridged
method
cyclohexadienone
reaction proceeds
Borylative
framework
borylative cyclization
2pin
tandem process
borylation
bicyclic products