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A General Strategy for the Stereoselective Synthesis of Pyrrole‐Fused Chiral Skeletons: [3+2] Cycloaddition with 2‐Nitro‐2,3‐Unsaturated Glycosides
Author(s) -
Jiang Nan,
Mei Yuling,
Yang Yu,
Dong Youxian,
Ding Zekun,
Zhang Jianbo
Publication year - 2021
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.202100795
Subject(s) - stereoselectivity , chemistry , cycloaddition , pyrrole , nucleophile , catalysis , carbene , organic chemistry , combinatorial chemistry , stereochemistry
In this study, a two‐step methodology was developed for the synthesis of chiral pyrroles from 2‐nitroglycals via Ferrier rearrangement and Barton‐Zard reaction under mild conditions without transition metal catalysts. The Ferrier rearrangement reaction of 2‐nitro‐glycals and a series of O ‐nucleophiles proceeded smoothly in the presence of N ‐heterocyclic carbene (NHC) catalyst and K 2 CO 3 which allowed the highly stereoselective synthesis of the diverse 2‐nitro‐2,3‐unsaturated glycosides in excellent yields. Subsequently, the rearrangement products were conveniently transformed into the desired chiral pyrroles by [3+2] cycloaddition (Barton‐Zard reaction) with isocyanoacetate in the presence of Cs 2 CO 3 . One‐pot strategy was also successfully demonstrated for the gram‐scale synthesis of one chiral pyrrole. This is the first report of stereoselective conversion from 2‐nitroglycals to chiral pyrrole.