Silver(I)-Catalyzed Dearomatization of Alkyne-Tethered Indoles: Divergent Synthesis of Spirocyclic Indolenines and Carbazoles

TY - JOUR

T1 - Silver(I)-Catalyzed Dearomatization of Alkyne-Tethered Indoles

T2 - Divergent Synthesis of Spirocyclic Indolenines and Carbazoles

AU - James, Michael J.

AU - Clubley, Rosa E.

AU - Palate, Kleopas Y.

AU - Procter, Thomas J.

AU - Wyton, Anthony C.

AU - O'Brien, Peter

AU - Taylor, Richard J K

AU - Unsworth, William P.

PY - 2015/8/21

Y1 - 2015/8/21

N2 - A high-yielding, divergent approach to generate either spirocyclic indolenines or carbazoles from a common indole-tethered propargyl alcohol precursor is described, with mechanistic insight provided. Either product can be obtained upon treatment with different Ag(I) catalysts at rt. An unexpected hydration reaction to afford (±)-actinopolymorphol B is also reported.

AB - A high-yielding, divergent approach to generate either spirocyclic indolenines or carbazoles from a common indole-tethered propargyl alcohol precursor is described, with mechanistic insight provided. Either product can be obtained upon treatment with different Ag(I) catalysts at rt. An unexpected hydration reaction to afford (±)-actinopolymorphol B is also reported.

UR - http://www.scopus.com/inward/record.url?scp=84941007120&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.5b02216

DO - 10.1021/acs.orglett.5b02216

M3 - Article

C2 - 26293968

SN - 1523-7060

VL - 17

SP - 4372

EP - 4375

JO - Organic Letters

JF - Organic Letters

IS - 17

ER -