Synthesis of Gluco‐Alkynones via a Carbonylative Coupling Reaction Using 1‐Iodoglucal-Reference-Cited by-同舟云学术

Synthesis of Gluco‐Alkynones via a Carbonylative Coupling Reaction Using 1‐Iodoglucal

Published:2023-09-15 Issue:35 Volume:8 Page:
ISSN:2365-6549
Container-title:ChemistrySelect
language:en
Short-container-title:ChemistrySelect

Author:

Paschoalin Caio¹,Toledo Mônica F. Z. J.¹,Veríssimo Dayane¹,Hornink Milene M.²,Pimenta Daniel C.³,Stefani Hélio A.¹^ORCID

Affiliation:

1. Departamento de Farmácia, Faculdade de Ciências Farmacêuticas Universidade de São Paulo Av. Prof. Lineu Prestes, 580 – Bl. 13 Superior 05508-000 São Paulo, SP Brazil

2. Departamento de Química, Instituto de Química Universidade de São Paulo Av. Prof. Lineu Preste, 748 05508-900 São Paulo, SP Brazil

3. Instituto Butantan Av. Vital Brasil, 1500 - Butantã, São Paulo - SP 05503-900 São Paulo, SP Brazil

Abstract

AbstractHerein, we report a simple and efficient synthesis of gluco‐alkynones obtained through the carbonylative coupling reaction of 1‐iodoglucal, catalyzed by palladium. A broad range of gluco‐alkynones were prepared with various aromatic aryl‐ and heteroaryl‐substituted alkynes. The reaction proved to be limiting for alkyl and propargyl acetylenes. Reactions occur within short times and in moderate to excellent yields.

Funder

Conselho Nacional de Desenvolvimento Científico e Tecnológico

Publisher

Wiley

Subject

General Chemistry

Reference62 articles.

2. A Convenient, Highly Efficient One-Pot Preparation of Peracetylated Glycals From Reducing Sugars

3. Glycals in Organic Synthesis: The Evolution of Comprehensive Strategies for the Assembly of Oligosaccharides and Glycoconjugates of Biological Consequence

4. Versatility of glycals in synthetic organic chemistry: coupling reactions, diversity oriented synthesis and natural product synthesis

5. Advances in the Synthesis of C-Glycosides from Glycals