Dearomatisation approaches to spirocyclic dienones via the electrophilic activation of alkynes

TY - JOUR

T1 - Dearomatisation approaches to spirocyclic dienones via the electrophilic activation of alkynes

AU - Clarke, Aimee K

AU - Liddon, John T R

AU - Cuthbertson, James D

AU - Taylor, Richard J K

AU - Unsworth, William Paul

N1 - © 2016, The Royal Society of Chemistry. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.

PY - 2017/1/7

Y1 - 2017/1/7

N2 - Two complementary dearomatising spirocyclisation protocols to generate spirocyclic dienones from anisole and phenol-tethered ynones are described, each proceeding via electrophilic alkyne activation. The first approach focuses on the spirocyclisation of para-substituted anisoles using either SnCl2·2H2O or Cu(OTf)2. The second approach, which enables the spirocyclisation of both ortho- and para-substituted phenols, uses silica-supported AgNO3 to generate similar scaffolds with much greater efficiency. Initial asymmetric studies are also outlined.

AB - Two complementary dearomatising spirocyclisation protocols to generate spirocyclic dienones from anisole and phenol-tethered ynones are described, each proceeding via electrophilic alkyne activation. The first approach focuses on the spirocyclisation of para-substituted anisoles using either SnCl2·2H2O or Cu(OTf)2. The second approach, which enables the spirocyclisation of both ortho- and para-substituted phenols, uses silica-supported AgNO3 to generate similar scaffolds with much greater efficiency. Initial asymmetric studies are also outlined.

U2 - 10.1039/c6ob02426b

DO - 10.1039/c6ob02426b

M3 - Article

C2 - 27901167

SN - 1477-0520

VL - 15

SP - 233

EP - 245

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 1

ER -