EnantiospecificSynthesis of Tetrahydroindolizinesfrom Spiro-cyclopropanecarboxylated Sugars

A facile two-step enantiospecific synthesis of 5,6,7,8-tetrahydroindolizine scaffolds has been developed via TMSOTf-promoted [3 + 2] cycloaddition between carbohydrate-derived spirocyclic donor–acceptor cyclopropanecarboxlates and alkyl/aryl nitriles followed by an intramolecular Mitsunobu reaction of the resulting chiral 2/5-(4-hydroxybutyl)pyrrole derivatives.

Publication Details

Journal
Figshare
Published
2025-01-15
DOI
https://doi.org/10.1021/acs.joc.4c02656.s001
Primary Topic
Mycorrhizal Fungi and Plant Interactions
Type
article
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article

EnantiospecificSynthesis of Tetrahydroindolizinesfrom Spiro-cyclopropanecarboxylated Sugars

Figshare
Mycorrhizal Fungi and Plant Interactions
article

EnantiospecificSynthesis of Tetrahydroindolizinesfrom Spiro-cyclopropanecarboxylated Sugars

article en

Abstract

A facile two-step enantiospecific synthesis of 5,6,7,8-tetrahydroindolizine scaffolds has been developed via TMSOTf-promoted [3 + 2] cycloaddition between carbohydrate-derived spirocyclic donor–acceptor cyclopropanecarboxlates and alkyl/aryl nitriles followed by an intramolecular Mitsunobu reaction of the resulting chiral 2/5-(4-hydroxybutyl)pyrrole derivatives.

Figshare
Clean water and sanitation
Openalex Percentile: Top 55%
Mycorrhizal Fungi and Plant Interactions
DOISourceOpenAlex
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EnantiospecificSynthesis of Tetrahydroindolizinesfrom Spiro-cyclopropanecarboxylated Sugars · Figshare (2025) | TGRS Research Map | TGRS