Dearomatizing Spiroannulation Reagents: Direct Access to Spirocycles from Indoles and Dihalides

TY - JOUR

T1 - Dearomatizing Spiroannulation Reagents

T2 - Direct Access to Spirocycles from Indoles and Dihalides

AU - Liddon, John T R

AU - Rossi-Ashton, James A

AU - Taylor, Richard J K

AU - Unsworth, William P

N1 - © 2018 American Chemical Society. 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 - 2018/5/10

Y1 - 2018/5/10

N2 - Unfunctionalized indoles can be directly converted into 3,3'-spirocyclic indolenines and indolines upon reaction with electrophilic dihalides in the presence of t-BuOK/BEt3. This double C-C bond forming reaction, which simultaneously generates a quaternary spirocyclic center, typically proceeds in high yield and has good functional group tolerance. In contrast to existing dearomatizing spirocyclization approaches, there is no need to prepare a prefunctionalized aromatic precursor, enabling faster access to valuable spirocyclic products from simple, commercially available aromatics in one step.

AB - Unfunctionalized indoles can be directly converted into 3,3'-spirocyclic indolenines and indolines upon reaction with electrophilic dihalides in the presence of t-BuOK/BEt3. This double C-C bond forming reaction, which simultaneously generates a quaternary spirocyclic center, typically proceeds in high yield and has good functional group tolerance. In contrast to existing dearomatizing spirocyclization approaches, there is no need to prepare a prefunctionalized aromatic precursor, enabling faster access to valuable spirocyclic products from simple, commercially available aromatics in one step.

KW - Journal Article

U2 - 10.1021/acs.orglett.8b01248

DO - 10.1021/acs.orglett.8b01248

M3 - Article

C2 - 29745671

SN - 1523-7060

JO - Organic Letters

JF - Organic Letters

ER -