TMSOTf-Mediated Cascade Synthesis of Hexahydropyrrolo[2,3-b]indoline Frameworks via the Meyer-Schuster Rearrangement

Rivonker, Shubham C.

doi:10.1021/acs.joc.6c00311

TMSOTf-Mediated Cascade Synthesis of Hexahydropyrrolo[2,3-b]indoline Frameworks via the Meyer-Schuster Rearrangement

2026-04-01

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AI

R

Rivonker, Shubham C.

S

Sthalam, Vinay Kumar

A

Ashok Kale

C

Choi, Yoon Mi

J

Jong Yeon Hwang

J

Jaemin, Cho

J

Jo, Nayeon

K

Kyeong Lee *

DOI：10.1021/acs.joc.6c00311

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Abstract

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TMSOTf-promoted cascade reaction between protected tryptamine and propargyl alcohol has been developed as an efficient strategy for the construction of hexahydropyrrolo[2,3-b]indoline frameworks. The transformation enables access to an expanded chemical space around this important scaffold via a Lewis-acid-driven annulation strategy. The protocol proceeds through a Meyer-Schuster rearrangement, followed by regioselective C-3 nucleophilic addition of the indole ring and subsequent 5-exo-trig cyclization. This method affords structurally diverse hexahydropyrrolo[2,3-b]indolines in moderate to good yields.

Keywords:

PROPARGYL ALCOHOLS

CONSTRUCTION

PYRROLOINDOLINES

CYCLIZATION

AMAUROMINE

INDOLES

TMSOTf-Mediated Cascade Synthesis of Hexahydropyrrolo[2,3-b]indoline Frameworks via the Meyer-Schuster Rearrangement

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