TMSOTf-Mediated Cascade Synthesis of Hexahydropyrrolo[2,3-b]indoline Frameworks via the Meyer-Schuster Rearrangement
  • Rivonker, Shubham C.
  • Sthalam, Vinay Kumar
  • Kale, Ashok
  • Choi, Yoon Mi
  • Hwang, Jong Yeon
  • ... Lee, Kyeong
  • 외 2명
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초록

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.

키워드

PROPARGYL ALCOHOLSCONSTRUCTIONPYRROLOINDOLINESCYCLIZATIONAMAUROMINEINDOLES
제목
TMSOTf-Mediated Cascade Synthesis of Hexahydropyrrolo[2,3-b]indoline Frameworks via the Meyer-Schuster Rearrangement
저자
Rivonker, Shubham C.Sthalam, Vinay KumarKale, AshokChoi, Yoon MiHwang, Jong YeonCho, JaeminJo, NayeonLee, Kyeong
DOI
10.1021/acs.joc.6c00311
발행일
2026-04
유형
Article; Early Access
저널명
Journal of Organic Chemistry