Silver(I)- or Copper(II)-Mediated Dearomatization of Aromatic Ynones: Direct Access to Spirocyclic Scaffolds

TY - JOUR

T1 - Silver(I)- or Copper(II)-Mediated Dearomatization of Aromatic Ynones

T2 - Direct Access to Spirocyclic Scaffolds

AU - James, Michael J.

AU - Cuthbertson, James D.

AU - O'Brien, Peter

AU - Taylor, Richard J K

AU - Unsworth, William P.

N1 - © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

PY - 2015/6/22

Y1 - 2015/6/22

N2 - A high-yielding silver(I)- or copper(II)-catalyzed dearomatizing spirocyclization strategy allows the conversion of simple aromatic compounds that contain ynone substituents, including indole, anisole, pyrrole, and benzofuran derivatives, into functionalized spirocyclic scaffolds. A high-yielding asymmetric variant furnishes spirocyclic indolenines in up to 89:11 e.r. Dearomatization: Simple achiral aromatic compounds that contain ynone substituents, including indole, anisole, pyrrole, and benzofuran derivatives, can be converted into complex chiral spirocyclic scaffolds. The silver(I)-catalyzed dearomatizing spirocyclization typically provides the products in more than 95 % yield and up to 89:11 e.r.

AB - A high-yielding silver(I)- or copper(II)-catalyzed dearomatizing spirocyclization strategy allows the conversion of simple aromatic compounds that contain ynone substituents, including indole, anisole, pyrrole, and benzofuran derivatives, into functionalized spirocyclic scaffolds. A high-yielding asymmetric variant furnishes spirocyclic indolenines in up to 89:11 e.r. Dearomatization: Simple achiral aromatic compounds that contain ynone substituents, including indole, anisole, pyrrole, and benzofuran derivatives, can be converted into complex chiral spirocyclic scaffolds. The silver(I)-catalyzed dearomatizing spirocyclization typically provides the products in more than 95 % yield and up to 89:11 e.r.

KW - asymmetric catalysis

KW - dearomatization

KW - indolenines

KW - silver

KW - spirocycles

UR - http://www.scopus.com/inward/record.url?scp=84935920605&partnerID=8YFLogxK

U2 - 10.1002/anie.201501812

DO - 10.1002/anie.201501812

M3 - Article

C2 - 25960013

SN - 1433-7851

VL - 54

SP - 7640

EP - 7643

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

IS - 26

ER -