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

2026-04-01

PRE

Rivonker, Shubham C.

Sthalam, Vinay Kumar

Ashok Kale

Choi, Yoon Mi

Jong Yeon Hwang

Jaemin, Cho

Jo, Nayeon

Kyeong Lee *

DOI：10.1021/acs.joc.6c00311

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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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