Synthesis of tetrahydropyrrolothiazoles through one-pot and four-component N,S-acetalation and decarboxylative [3+2] cycloaddition

Xiaoming Ma; Weiqi Qiu; Li Liu; Xiaofeng Zhang; John Mark Awad; Jason Evans; Wei Zhang

doi:10.1016/j.gresc.2020.11.001

Synthesis of tetrahydropyrrolothiazoles through one-pot and four-component N,S-acetalation and decarboxylative [3+2] cycloaddition

Xiaoming Ma
, Weiqi Qiu
, Li Liu
, Xiaofeng Zhang
, John Mark Awad
, Jason Evans
, Wei Zhang

Chemistry

Changzhou University
University of Massachusetts Boston
Harvard University
Broad Institute

Research output: Contribution to journal › Article › peer-review

Abstract

A four-component and one-pot synthesis involving N,S-acetalation of aldehydes with cysteine followed by the reaction with second aldehydes for decarboxylative [3 + 2] cycloaddition with maleimides is developed for stereoselective synthesis of tetrahydropyrrolothiazoles. High synthetic efficiency, using EtOH as solvent and catalyst, and only releasing CO₂ and H₂O as byproducts make this method favorable in green metrics analysis.

Original language	English
Pages (from-to)	74-77
Number of pages	4
Journal	Green Synthesis and Catalysis
Volume	2
Issue number	1
DOIs	https://doi.org/10.1016/j.gresc.2020.11.001
State	Published - Feb 2021

ASJC Scopus Subject Areas

Biotechnology
Catalysis

Keywords

Green metrics
N,S-acetal
One-pot
Tetrahydropyrrolothiazoles
[3+2] cycloaddition

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10.1016/j.gresc.2020.11.001

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title = "Synthesis of tetrahydropyrrolothiazoles through one-pot and four-component N,S-acetalation and decarboxylative [3+2] cycloaddition",

abstract = "A four-component and one-pot synthesis involving N,S-acetalation of aldehydes with cysteine followed by the reaction with second aldehydes for decarboxylative [3 + 2] cycloaddition with maleimides is developed for stereoselective synthesis of tetrahydropyrrolothiazoles. High synthetic efficiency, using EtOH as solvent and catalyst, and only releasing CO2 and H2O as byproducts make this method favorable in green metrics analysis.",

keywords = "Green metrics, N,S-acetal, One-pot, Tetrahydropyrrolothiazoles, [3+2] cycloaddition",

author = "Xiaoming Ma and Weiqi Qiu and Li Liu and Xiaofeng Zhang and Awad, \{John Mark\} and Jason Evans and Wei Zhang",

note = "Publisher Copyright: {\textcopyright} 2020 The Authors",

year = "2021",

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doi = "10.1016/j.gresc.2020.11.001",

language = "English",

volume = "2",

pages = "74--77",

journal = "Green Synthesis and Catalysis",

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TY - JOUR

T1 - Synthesis of tetrahydropyrrolothiazoles through one-pot and four-component N,S-acetalation and decarboxylative [3+2] cycloaddition

AU - Ma, Xiaoming

AU - Qiu, Weiqi

AU - Liu, Li

AU - Zhang, Xiaofeng

AU - Awad, John Mark

AU - Evans, Jason

AU - Zhang, Wei

PY - 2021/2

Y1 - 2021/2

N2 - A four-component and one-pot synthesis involving N,S-acetalation of aldehydes with cysteine followed by the reaction with second aldehydes for decarboxylative [3 + 2] cycloaddition with maleimides is developed for stereoselective synthesis of tetrahydropyrrolothiazoles. High synthetic efficiency, using EtOH as solvent and catalyst, and only releasing CO2 and H2O as byproducts make this method favorable in green metrics analysis.

AB - A four-component and one-pot synthesis involving N,S-acetalation of aldehydes with cysteine followed by the reaction with second aldehydes for decarboxylative [3 + 2] cycloaddition with maleimides is developed for stereoselective synthesis of tetrahydropyrrolothiazoles. High synthetic efficiency, using EtOH as solvent and catalyst, and only releasing CO2 and H2O as byproducts make this method favorable in green metrics analysis.

KW - Green metrics

KW - N,S-acetal

KW - One-pot

KW - Tetrahydropyrrolothiazoles

KW - [3+2] cycloaddition

UR - https://www.scopus.com/pages/publications/85112690754

UR - https://www.scopus.com/pages/publications/85112690754#tab=citedBy

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DO - 10.1016/j.gresc.2020.11.001

M3 - Article

AN - SCOPUS:85112690754

SN - 2666-5549

VL - 2

SP - 74

EP - 77

JO - Green Synthesis and Catalysis

JF - Green Synthesis and Catalysis

IS - 1

ER -

Synthesis of tetrahydropyrrolothiazoles through one-pot and four-component N,S-acetalation and decarboxylative [3+2] cycloaddition

Abstract

ASJC Scopus Subject Areas

Keywords

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