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

Michael J. James; Rosa E. Clubley; Kleopas Y. Palate; Thomas J. Procter; Anthony C. Wyton; Peter O’brien; Richard J. K. Taylor; William. P. Unsworth

doi:10.1021/acs.orglett.5b02216

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

Michael J. James, Rosa E. Clubley, Kleopas Y. Palate, Thomas J. Procter, Anthony C. Wyton, Peter O’brien, Richard J. K. Taylor, William. P. Unsworth

Organic Chemistry Group

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English
Pages (from-to)	4372-4375
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	17
DOIs	https://doi.org/10.1021/acs.orglett.5b02216
Publication status	Published - 21 Aug 2015

Access to Document

10.1021/acs.orglett.5b02216

https://pubs.acs.org/doi/10.1021/acs.orglett.5b02216

Cite this

@article{6e127f7d4e8746a380f5610e0614bac1,

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

abstract = "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.",

author = "James, {Michael J.} and Clubley, {Rosa E.} and Palate, {Kleopas Y.} and Procter, {Thomas J.} and Wyton, {Anthony C.} and Peter O{\textquoteright}brien and Taylor, {Richard J. K.} and Unsworth, {William. P.}",

year = "2015",

month = aug,

day = "21",

doi = "10.1021/acs.orglett.5b02216",

language = "English",

volume = "17",

pages = "4372--4375",

journal = "Organic Letters",

issn = "1523-7052",

publisher = "American Chemical Society",

number = "17",

}

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.

U2 - 10.1021/acs.orglett.5b02216

DO - 10.1021/acs.orglett.5b02216

M3 - Article

SN - 1523-7052

VL - 17

SP - 4372

EP - 4375

JO - Organic Letters

JF - Organic Letters

IS - 17

ER -

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

Abstract

Access to Document

Fingerprint

Cite this